3,6-METHANO-1H-PYRROLO[3,2-b]PYRIDINE AND 3,6-METHANO-1H-PYRROLO[3,2-c]PYRIDINE COMPOUNDS AND MEDICAMENTS USING SAME

ABSTRACT

The present disclosure provides a compound that is useful for the treatment and prophylaxis of rabies. The present disclosure provides a compound represented by formula XXIIF or formula XXIIB:wherein R1, R2A, R2B, R3, and R4 are defined in the specification, a solvent, or a pharmaceutically acceptable salt thereof, use of such a compound, solvate, or pharmaceutically acceptable salt thereof for the treatment or prophylaxis of rabies and cancer, a pharmaceutical composition comprising such a compound, solvate, or pharmaceutically acceptable salt thereof, and a method for the treatment or prophylaxis of rabies and cancer using the same.

TECHNICAL FIELD

The present disclosure relates to a novel fused tricyclic compound thatis useful as a medicament, an enantiomer thereof, or a pharmaceuticallyacceptable salt thereof, or a solvate thereof. More specifically, thepresent disclosure relates to a pharmaceutical composition comprisingthe fused tricyclic compound or an enantiomer thereof, or apharmaceutically acceptable salt thereof, or a solvate thereof. Thepresent disclosure also relates to a therapeutic agent comprising thefused tricyclic compound or an enantiomer thereof, or a pharmaceuticallyacceptable salt thereof, or a solvate thereof.

BACKGROUND ART

Rabies is an infection induced by a rabies virus. The mortality afterthe onset in humans is almost 100%. While over 15 million peopleworldwide are vaccinated post-exposure for the prophylaxis of rabiesevery year, the worldwide number of fatalities due to rabies is about55000 annually. An effective therapeutic method for rabies still has notbeen established. There is still a demand for the establishment thereof.

SUMMARY OF INVENTION Solution to Problem

The present disclosure provides a compound and a method for thetreatment of rabies and other diseases.

The present disclosure was completed by the inventors from finding thatcompounds represented by the following formula IF, IB, IIF, BB, XXIF,XXIB, XXIIF, or XXIIB and the structural formulas related thereto, or apharmaceutically acceptable salt thereof (hereinafter, also referred toas “the compound(s) of the present disclosure” or “the presentcompound(s)”) can achieve the objects as a result of diligent study.

The present disclosure provides the following items.

[Item 1]

A compound represented by formula XXIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₃, and R₄ are each independently hydrogen, an optionallysubstituted hydrocarbon group, an optionally substituted heterocycle,optionally substituted carbonyl, or an optionally substituted functionalgroup, and

R_(2A) and R_(2B) are each independently hydrogen, an optionallysubstituted hydrocarbon group, an optionally substituted heterocycle,optionally substituted carbonyl, or an optionally substituted functionalgroup, or R_(2A) and R_(2B), together with the nitrogen atom to whichthey are attached, form a heterocycle, wherein the heterocycles are eachindependently and optionally substituted.

[Item 1B]

The compound represented by formula XXIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereofaccording to item 1, wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedalkyl, optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl,

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkynyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 2]

A compound represented by formula XXIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₃, and R₄ are each independently hydrogen, an optionallysubstituted hydrocarbon group, an optionally substituted heterocycle,optionally substituted carbonyl, or an optionally substituted functionalgroup,

R_(2A) and R_(2B) are each independently hydrogen, an optionallysubstituted hydrocarbon group, an optionally substituted heterocycle,optionally substituted carbonyl, or an optionally substituted functionalgroup, or R_(2A) and R_(2B), together with the nitrogen atom to whichthey are attached, form a heterocycle, wherein the heterocycles are eachindependently and optionally substituted.

[Item 2B]

The compound represented by formula XXIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereofaccording to item 2, wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedalkyl, optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl,

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkynyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 3]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl,heteroaryl, and carbonyl of R₁, R₃, and R₄ are each independently andoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group I,and

the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl,heteroaryl, carbonyl, and the non-aryl heterocycle and the heteroarylring of R_(2A) and R_(2B) are each independently and optionallysubstituted with one to the maximum substitutable number of the same ordifferent sub stituents selected from sub stituent group I.

[Item 4]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedalkyl, optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 4B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedC₁₋₁₂ alkyl, optionally substituted C₃₋₁₀ cycloalkyl, optionallysubstituted 5- to 10-membered heterocycloalkyl, optionally substitutedC₆₋₁₀ aryl, optionally substituted 5- to 10-membered heteroaryl, oroptionally substituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₃₋₁₀ cycloalkyl,optionally substituted 5- to 10-membered heterocycloalkyl, optionallysubstituted C₆₋₁₀ aryl, optionally substituted 5- to 10-memberedheteroaryl, or optionally substituted carbonyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 5]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedalkyl, optionally substituted arylalkyl, optionally substitutedcycloalkyl, optionally substituted heterocycloalkyl, formyl, optionallysubstituted alkylcarbonyl, optionally substituted alkoxycarbonyl,optionally substituted arylcarbonyl, optionally substitutedaryloxycarbonyl, optionally substituted heteroarylcarbonyl, optionallysubstituted heteroaryloxycarbonyl, optionally substitutedcycloalkylcarbonyl, optionally substituted cycloalkyloxycarbonyl,optionally substituted heterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁, R₃, and R₄ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group II,and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl, formyl,optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, optionally substituted heteroarylcarbonyl,optionally substituted heteroaryloxycarbonyl, optionally substitutedcycloalkylcarbonyl, optionally substituted cycloalkyloxycarbonyl,optionally substituted heterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R_(2A) and R_(2B) areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group II,or R_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a 5- to 6-membered non-aryl heterocycle or heteroarylring, wherein the non-aryl heterocycle and the heteroaryl ring areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group II.

[Item 5B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedC₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl, optionallysubstituted C₃₋₁₀ cycloalkyl, optionally substituted 5- to 10-memberedheterocycloalkyl, formyl, optionally substituted C₁₋₁₂ alkylcarbonyl,optionally substituted C₁₋₁₂ alkoxycarbonyl, optionally substitutedC₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀ aryloxycarbonyl,optionally substituted 5- to 10-membered heteroarylcarbonyl, optionallysubstituted 5- to 10-membered heteroaryloxycarbonyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbonyl, optionally substituted C₃₋₁₀cycloalkyloxycarbonyl, optionally substituted 5- to 10-memberedheterocycloalkylcarbonyl, optionally substituted 5- to 10-memberedheterocycloalkyloxycarbonyl, carbamoyl, optionally substituted C₁₋₁₂alkylcarbamoyl, optionally substituted C₁₋₁₂ alkoxycarbamoyl, optionallysubstituted C₆₋₁₀ arylcarbamoyl, optionally substituted 5- to10-membered heteroarylcarbamoyl, optionally substituted C₃₋₁₀cycloalkylcarbamoyl, or optionally substituted 5- to 10-memberedheterocycloalkylcarbamoyl, wherein the groups of R₁, R₃, and R₄ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group III,and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl,optionally substituted C₃₋₁₀ cycloalkyl, optionally substituted 5- to10-membered heterocycloalkyl, formyl, optionally substituted C₁₋₁₂alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl, optionallysubstituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted 5- to 10-memberedheteroarylcarbonyl, optionally substituted 5- to 10-memberedheteroaryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R_(2A) andR_(2B) are optionally substituted with one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup III, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a 5- to 6-membered non-aryl heterocycle,wherein the non-aryl heterocycle is optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from substituent group V.

[Item 6]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen, optionally substituted alkyl,optionally substituted arylalkyl, optionally substituted cycloalkyl,formyl, optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, optionally substituted cycloalkylcarbonyl,optionally substituted cycloalkyloxycarbonyl, optionally substitutedheterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₄ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group III.

[Item 6B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen, optionally substituted C₁₋₁₂alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl, optionallysubstituted C₃₋₁₀ cycloalkyl, formyl, optionally substituted C₁₋₁₂alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl, optionallysubstituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R₁ and R₄are optionally substituted with one to the maximum substitutable numberof the same or different substituents selected from substituent groupIII.

[Item 7]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen, optionally substituted alkyl,optionally substituted arylalkyl, formyl, optionally substitutedalkylcarbonyl, optionally substituted alkoxycarbonyl, optionallysubstituted arylcarbonyl, optionally substituted aryloxycarbonyl,carbamoyl, or optionally substituted alkylcarbamoyl, wherein the groupsof R₁ and R₄ are optionally substituted with one to the maximumsubstitutable number of the same or different sub stituents selectedfrom sub stituent group III.

[Item 7B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen, optionally substituted C₁₋₁₂alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl, formyl, optionallysubstituted C₁₋₁₂ alkylcarbonyl, optionally substituted C₁₋₁₂alkoxycarbonyl, optionally substituted C₆₋₁₀ arylcarbonyl, optionallysubstituted C₆₋₁₀ aryloxycarbonyl, carbamoyl, or optionally substitutedC₁₋₁₂ alkylcarbamoyl, wherein the groups of R₁ and R₄ are optionallysubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from substituent group III.

[Item 8]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen; alkyl; alkyl substituted withone to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amino, substitutedamino, substituted oxy, substituted carbonyl, cycloalkyl, andsubstituted cycloalkyl; arylalkyl; arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, alkyl, substituted alkyl,hydroxy, substituted oxy, amino, substituted amino, and nitro; formyl;substituted carbonyl; or substituted oxycarbonyl, wherein thesubstituted amino, substituted oxy, substituted alkyl, substitutedcarbonyl, substituted cycloalkyl, substituted carbonyl, and substitutedoxycarbonyl in R₁ and R₄ each independently have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 8B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen; C₁₋₁₂ alkyl; C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of amino,substituted amino, substituted oxy, substituted carbonyl, C₃₋₁₀cycloalkyl, and substituted C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl;C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of halogen, C₁₋₆ alkyl, substituted alkyl, hydroxy,substituted oxy, amino, substituted amino, and nitro; formyl;substituted carbonyl; or substituted oxycarbonyl, wherein thesubstituted amino, substituted oxy, substituted alkyl, substitutedcarbonyl, substituted cycloalkyl, substituted carbonyl, and substitutedoxycarbonyl in R₁ and R₄ each independently have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 9]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen; alkyl; alkyl substituted withone to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino, alkoxy,alkoxycarbonyl, carbamoyl, carboxy, hydroxy, trialkylsilyloxy, andcycloalkyl; arylalkyl; arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,amino, substituted amino, nitro, and hydroxy; formyl; alkylcarbonyl;arylalkylcarbonyl; arylalkyloxycarbonyl; alkoxycarbonyl; arylcarbonyl;aryloxycarbonyl; carbamoyl; alkylcarbamoyl; or arylalkylcarbamoyl,wherein the substituted amino each independently have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 9B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₄ are each independently hydrogen; C₁₋₁₂ alkyl; C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting ofamidinoamino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, carbamoyl, carboxy,hydroxy, tri-C₁₋₆ alkylsilyloxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆alkyl; C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, amino, substituted amino, nitro, and hydroxy;formyl; C₁₋₁₂ alkylcarbonyl; C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl; C₆₋₁₀ arylC₁₋₆ alkyloxycarbonyl; C₁₋₁₂ alkoxycarbonyl; C₆₋₁₀ arylcarbonyl; C₆₋₁₀aryloxycarbonyl; carbamoyl; C₁₋₁₂ alkylcarbamoyl; or C₆₋₁₀ aryl C₁₋₆alkylcarbamoyl, wherein the substituted amino have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 10]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is hydrogen; alkyl; alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amino, substituted amino, carboxy, substitutedoxycarbonyl, carbamoyl, substituted aminocarbonyl, hydroxy, substitutedoxy, cycloalkyl, and substituted cycloalkyl; arylalkyl; or arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,alkyl, substituted alkyl, carboxy, substituted oxycarbonyl, hydroxy, andsubstituted oxy, wherein the substituted amino, substituted oxy,substituted oxycarbonyl, substituted aminocarbonyl, substituted alkyl,substituted cycloalkyl, substituted carbonyl, and substitutedoxycarbonyl in R₃ each independently have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 11]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is hydrogen; alkyl; alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, alkoxycarbonyl, carbamoyl,carboxy, hydroxy, trialkylsilyloxy, amino, alkoxycarbonylamino, andcycloalkyl; arylalkyl; or arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, alkyl, alkoxycarbonyl, and hydroxy.

[Item 11B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is hydrogen; C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, C₁₋₆ alkoxycarbonyl,carbamoyl, carboxy, hydroxy, tri-C₁₋₆ alkylsilyloxy, amino, C₁₋₆alkoxycarbonylamino, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; orC₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximum substitutablenumber of the same or different sub stituents selected from the groupconsisting of halogen, C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyl, and hydroxy.

[Item 12]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) and R_(2B) are each independently hydrogen; alkyl; alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of formyl,substituted carbonyl, hydroxy, substituted oxy, amino, substitutedamino, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, andsubstituted heterocycloalkyl; arylalkyl; arylalkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, alkyl,substituted alkyl, hydroxy, and substituted oxy; heteroarylalkyl;substituted heteroarylalkyl; cycloalkyl; or substituted cycloalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substitutedheteroarylalkyl, and substituted alkyl in R_(2A) and R_(2B) eachindependently have one to the maximum substitutable number of the sameor different sub stituents selected from sub stituent group IV, orR_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a non-aryl heterocycle, wherein the non-aryl heterocycleis optionally substituted with one to the maximum substitutable numberof the same or different substituents selected from substituent groupVI.

[Item 13]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) and R_(2B) are each independently hydrogen; alkyl; alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting ofamidinoamino, alkoxy, alkoxycarbonyl, carbamoyl, carboxy, hydroxy,amino, alkoxycarbonylamino, cycloalkyl, and heterocycloalkyl; arylalkyl;arylalkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, alkyl, haloalkyl, alkoxy, and hydroxy; heteroarylalkyl;alkoxycarbonyl-substituted heteroarylalkyl; or cycloalkyl, or R_(2A) andR_(2B), together with the nitrogen atom to which they are attached, forma 5- to 6-membered non-aryl heterocycle, wherein the non-arylheterocycle is optionally substituted with one or up to the maximumsubstitutable number of the same or different substituents selected fromsub stituent group VI.

[Item 13B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) and R_(2B) are each independently hydrogen; C₁₋₁₂ alkyl; C₁₋₁₂alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofamidinoamino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, carbamoyl, carboxy,hydroxy, amino, C₁₋₆ alkoxycarbonylamino, C₃₋₁₀ cycloalkyl, and 5- to10-membered heterocycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; C₆₋₁₀ aryl C₁₋₆alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhalogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, and hydroxy; 5- to10-membered heteroaryl C₁₋₆ alkyl; C₁₋₆ alkoxycarbonyl-substituted 5- to10-membered heteroaryl C₁₋₆ alkyl; or C₃₋₁₀ cycloalkyl, or R_(2A) andR_(2B), together with the nitrogen atom to which they are attached, forma 5- to 6-membered non-aryl heterocycle, wherein the non-arylheterocycle is optionally substituted with one or up to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group VI.

[Item 14]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is alkyl; alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of amidinoamino, carbamoyl, carboxy, hydroxy, and cycloalkyl;arylalkyl; or arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, alkyl, haloalkyl, alkoxy, substitutedamino, and hydroxy, wherein the substituted amino has one to the maximumsubstitutable number of the same or different substituents selected fromsub stituent group IV.

[Item 14B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, carbamoyl, carboxy, hydroxy, andC₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; or C₆₋₁₀ aryl C₁₋₆ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, substituted amino, and hydroxy,wherein the substituted amino has one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup IV.

[Item 15]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) is hydrogen, and R_(2B) is alkyl; alkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, carbamoyl, carboxy,hydroxy, and cycloalkyl; arylalkyl; arylalkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of halogen, alkyl, haloalkyl, alkoxy,and hydroxy; or cycloalkyl.

[Item 15B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) is hydrogen, and R_(2B) is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino,carbamoyl, carboxy, hydroxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆alkyl; C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, and hydroxy; or C₃₋₁₀ cycloalkyl.

[Item 16]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is alkyl; alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of amidinoamino, carbamoyl, carboxy, hydroxy, and cycloalkyl;arylalkyl; or arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of alkyl and hydroxy.

[Item 16B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, carbamoyl, carboxy, hydroxy, andC₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; or C₆₋₁₀ aryl C₁₋₆ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of C₁₋₆ alkyland hydroxy.

[Item 17]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, alkyl, alkylcarbonyl, arylalkylcarbonyl,arylalkyloxycarbonyl, alkoxycarbonyl, carbamoyl, or arylalkylcarbamoyl.

[Item 17B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, C₁₋₁₂ alkyl, C₁₋₁₂ alkylcarbonyl, C₆₋₁₀ aryl C₁₋₆alkylcarbonyl, C₆₋₁₀ aryl C₁₋₆ alkyloxycarbonyl, C₁₋₁₂ alkoxycarbonyl,carbamoyl, or C₆₋₁₀ aryl C₁₋₆ alkylcarbamoyl.

[Item 17C]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is hydrogen, methyl, ethyl, isobutyl, isopentyl, amidinoaminopropyl,tert-butoxyethyl, tert-butoxypropyl, (tert-butoxycarbonyl)ethyl,carbamoylmethyl, carboxyethyl, hydroxyethyl, hydroxypropyl,cyclopentylmethyl, cyclohexylmethyl, benzyl, phenylethyl,naphthalenylmethyl, fluorobenzyl, chlorobenzyl, dichlorobenzyl,methylbenzyl, tert-butylbenzyl, (trifluoromethyl)benzyl, methoxybenzyl,ethoxybenzyl, tert-butoxybenzyl, aminobenzyl,(cyclopentylcarbonylamino)benzyl, (cyclopentylmethylamino)benzyl,(dimethylamino)benzyl, (carbamoylethylcarbonylamino)benzyl,(carboxyethylcarbonylamino)benzyl, nitrobenzyl, hydroxybenzyl,3-methylbutanoyl, isobutylcarbonyl, 2-phenylacetyl,isopropyloxycarbonyl, benzoyl, or phenyloxycarbonyl.

[Item 17D]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) is hydrogen, R_(2B) is methyl, isopropyl, isobutyl, n-pentyl,isopentyl, n-hexyl, heptyl, amidinoaminopropyl, tert-butoxyethyl,tert-butoxycarbonylmethyl, carbamoylmethyl, carbamoylethyl,carboxyethyl, hydroxyethyl, aminobutyl,((tert-butoxycarbonyl)amino)butyl, cyclohexylmethyl,(tetrahydro-2H-pyran-2-yl)methyl, benzyl, phenylethyl,naphthalenylmethyl, naphthalenylethyl, fluorobenzyl, chlorobenzyl,dichlorobenzyl, (fluorophenyl)ethyl, methylbenzyl,(trifluoromethyl)benzyl, methoxybenzyl, tert-butoxybenzyl,hydroxybenzyl, α-hydroxymethylphenethyl, β-hydroxyphenethyl,pyridinylmethyl, (1H-indol-3-yl)ethyl,(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, cyclopentyl, orcyclohexyl, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a pyrrolidine ring or piperidine ring.

[Item 17E]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is n-propyl, isobutyl, isopentyl, amidinoaminopropyl,(methoxycarbonyl)ethyl, (tert-butoxycarbonyl)ethyl, carbamoylmethyl,carboxyethyl, hydroxymethyl, hydroxyethyl, (tert-butyldimethylsilyloxy)ethyl, aminobutyl, ((tert-butoxycarbonyl)amino)butyl,cyclohexylmethyl, cyclohexylethyl, benzyl, phenylethyl, phenylpropyl,phenylbutyl, naphthalenylmethyl, naphthalenylethyl, chlorobenzyl,methylbenzyl, (methylphenyl)ethyl, (isopropylphenyl)ethyl, orhydroxybenzyl.

[Item 17F]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, methyl, ethyl, isobutyl, formyl, acetyl,3-methylbutanoyl, 2-phenylacetyl, methoxycarbonyl, ethoxycarbonyl,2-methylpropyloxycarbonyl, tert-butoxycarbonyl, benzoyl, benzyl,benzyloxycarbonyl, aminocarbonyl, N-benzylaminocarbonyl,propylcarbamoyl, N-isobutylaminocarbonyl, or N-benzylaminocarbonyl.

[Item 17G]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the compound is a compound selected from the group consisting ofcompound numbers IB-1 to IB-995 and IF-1 to IF-931.

[Item 18]

A compound represented by formula XXIIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁ and R₃ are each independently hydrogen, optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkynyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 19]

A compound represented by formula XXIIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁ and R₃ are each independently hydrogen, optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkynyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 20]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl,heteroaryl, and carbonyl of R₁ and R₃ are each independently andoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from substituent group I,and

the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl,heteroaryl, carbonyl, and the non-aryl heterocycle and the heteroarylring of R_(2A) and R_(2B) are each independently and optionallysubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from substituent group I.

[Item 21]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently hydrogen, optionally substituted alkyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

[Item 22]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently hydrogen, optionally substituted alkyl,optionally substituted arylalkyl, optionally substituted cycloalkyl,optionally substituted heterocycloalkyl, formyl, optionally substitutedalkylcarbonyl, optionally substituted alkoxycarbonyl, optionallysubstituted arylcarbonyl, optionally substituted aryloxycarbonyl,optionally substituted heteroarylcarbonyl, optionally substitutedheteroaryloxycarbonyl, optionally substituted cycloalkylcarbonyl,optionally substituted cycloalkyloxycarbonyl, optionally substitutedheterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from sub stituent group II,and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl, formyl,optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, optionally substituted heteroarylcarbonyl,optionally substituted heteroaryloxycarbonyl, optionally substitutedcycloalkylcarbonyl, optionally substituted cycloalkyloxycarbonyl,optionally substituted heterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R_(2A) and R_(2B) areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group II,or R_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a 5- to 6-membered non-aryl heterocycle, wherein thenon-aryl heterocycle is optionally substituted with one to the maximumsubstitutable number of the same or different substituents selected fromsub stituent group II.

[Item 23]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently hydrogen, optionally substituted C₁₋₁₂alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl, optionallysubstituted C₃₋₁₀ cycloalkyl, optionally substituted 5- to 10-memberedheterocycloalkyl, formyl, optionally substituted C₁₋₁₂ alkylcarbonyl,optionally substituted C₁₋₁₂ alkoxycarbonyl, optionally substitutedC₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀ aryloxycarbonyl,optionally substituted 5- to 10-membered heteroarylcarbonyl, optionallysubstituted 5- to 10-membered heteroaryloxycarbonyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbonyl, optionally substituted C₃₋₁₀cycloalkyloxycarbonyl, optionally substituted 5- to 10-memberedheterocycloalkylcarbonyl, optionally substituted 5- to 10-memberedheterocycloalkyloxycarbonyl, carbamoyl, optionally substituted C₁₋₁₂alkylcarbamoyl, optionally substituted C₁₋₁₂ alkoxycarbamoyl, optionallysubstituted C₆₋₁₀ arylcarbamoyl, optionally substituted 5- to10-membered heteroarylcarbamoyl, optionally substituted C₃₋₁₀cycloalkylcarbamoyl, or optionally substituted 5- to 10-memberedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group III,and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl,optionally substituted C₃₋₁₀ cycloalkyl, optionally substituted 5- to10-membered heterocycloalkyl, formyl, optionally substituted C₁₋₁₂alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl, optionallysubstituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted 5- to 10-memberedheteroarylcarbonyl, optionally substituted 5- to 10-memberedheteroaryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R_(2A) andR_(2B) are optionally substituted with one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup III, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a 5- to 6-membered non-aryl heterocycle,wherein the non-aryl heterocycle is optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from substituent group III.

[Item 24]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently hydrogen, optionally substituted alkyl,optionally substituted arylalkyl, optionally substituted cycloalkyl,formyl, optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, optionally substituted cycloalkylcarbonyl,optionally substituted cycloalkyloxycarbonyl, optionally substitutedheterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group III.

[Item 25B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently hydrogen, optionally substituted C₁₋₁₂alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl, optionallysubstituted C₃₋₁₀ cycloalkyl, formyl, optionally substituted C₁₋₁₂alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl, optionallysubstituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃are optionally substituted with one to the maximum substitutable numberof the same or different substituents selected from substituent groupIII.

[Item 25]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is hydrogen; alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amino, substituted amino, hydroxy, substitutedoxy, formyl, substituted carbonyl, cycloalkyl, and substitutedcycloalkyl; arylalkyl; arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, alkyl, substituted alkyl, hydroxy,substituted oxy, amino, substituted amino, and nitro; formyl; orsubstituted carbonyl, wherein the substituted amino, substituted oxy,substituted carbonyl, substituted cycloalkyl, and substituted alkyl inR₁ each independently have one to the maximum substitutable number ofthe same or different substituents selected from substituent group IV.

[Item 26]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is hydrogen; alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, alkoxycarbonyl-substitutedamidinoamino, alkoxy, alkoxycarbonyl, carbamoyl, carboxy, hydroxy,trialkylsilyloxy, and cycloalkyl; arylalkyl; arylalkyl substituted withone to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, alkyl,haloalkyl, alkoxy, haloalkoxy, amino, substituted amino, nitro, andhydroxy; formyl; alkylcarbonyl; arylalkylcarbonyl; alkoxycarbonyl;arylcarbonyl; aryloxycarbonyl; carbamoyl; alkylcarbamoyl; orarylalkylcarbamoyl, wherein the substituted amino has one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 27B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is hydrogen; C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, C₁₋₆alkoxycarbonyl-substituted amidinoamino, C₁₋₆ alkoxy, C₁₋₆alkoxycarbonyl, carbamoyl, carboxy, hydroxy, tri-C₁₋₆ alkylsilyloxy, andC₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; C₆₋₁₀ aryl C₁₋₆ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, amino,substituted amino, nitro, and hydroxy; formyl; C₁₋₁₂ alkylcarbonyl;C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl; C₁₋₁₂ alkoxycarbonyl; C₆₋₁₀ arylcarbonyl;C₆₋₁₀ aryloxycarbonyl; carbamoyl; C₁₋₁₂ alkylcarbamoyl; or C₆₋₁₀ arylC₁₋₆ alkylcarbamoyl, wherein the substituted amino has one to themaximum substitutable number of the same or different substituentsselected from substituent group IV.

[Item 27C]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, C₁₋₆ alkoxycarbonyl-substitutedamidinoamino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, carbamoyl, carboxy,hydroxy, tri-C₁₋₆ alkylsilyloxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆alkyl; or C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, amino, substituted amino, nitro, and hydroxy,wherein the substituted amino has one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup IV.

[Item 28]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is hydrogen; alkyl; formyl; substituted carbonyl; alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of hydroxy, substitutedoxy, substituted carbonyl, amino, substituted amino, cycloalkyl,substituted cycloalkyl, heterocycloalkyl, and substitutedheterocycloalkyl; arylalkyl; arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy,substituted oxy, amino, substituted amino, alkyl, and substituted alkyl;heteroarylalkyl; or substituted heteroarylalkyl, wherein the substitutedcarbonyl, substituted oxy, substituted amino, substituted cycloalkyl,substituted heterocycloalkyl, substituted alkyl, and substitutedheteroarylalkyl in R₃ each independently have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 29B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is hydrogen; alkyl; formyl; alkylcarbonyl; arylalkylcarbonyl; alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of hydroxy,trialkylsilyloxy, alkoxy, alkoxycarbonyl, alkoxycarbonylamino,cycloalkyl, carboxy, amino, amidinoamino, alkoxycarbonyl-substitutedamidinoamino, carbamoyl, and heterocycloalkyl; arylalkyl; arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, amino, monoalkylamino, dialkylamino, alkyl, haloalkyl,alkoxy, haloalkoxy, carboxyalkylcarbonylamino,carbamoylalkylcarbonylamino, cycloalkylcarbonylamino, andcycloalkylalkylamino; heteroarylalkyl; or alkoxycarbonyl-substitutedheteroarylalkyl.

[Item 29C]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is hydrogen; C₁₋₁₂ alkyl; formyl; C₁₋₆ alkylcarbonyl; C₆₋₁₀ aryl C₁₋₆alkylcarbonyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of hydroxy, tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy,C₁₋₆ alkoxycarbonyl, C₁₋₆ alkoxycarbonylamino, C₃₋₆ cycloalkyl, carboxy,amino, amidinoamino, C₁₋₆ alkoxycarbonyl-substituted amidinoamino,carbamoyl, and 5- to 6-membered heterocycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl;C₆₋₁₀ aryl C₁₋₁₂ alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of halogen, nitro, hydroxy, amino, mono-C₁₋₆ alkylamino,di-C₁₋₆ alkylamino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆haloalkoxy, carboxy C₁₋₆ alkylcarbonylamino, carbamoyl C₁₋₆alkylcarbonylamino, C₃₋₆ cycloalkylcarbonylamino, and C₃₋₆ cycloalkylC₁₋₆ alkylamino; 5- to 10-membered heteroaryl C₁₋₆ alkyl; or C₁₋₆alkoxycarbonyl-substituted 5- to 10-membered heteroaryl C₁₋₆ alkyl.

[Item 29D]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of hydroxy, tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy,C₁₋₆ alkoxycarbonyl, C₁₋₆ alkoxycarbonylamino, C₃₋₆ cycloalkyl, carboxy,amino, amidinoamino, C₁₋₆ alkoxycarbonyl-substituted amidinoamino,carbamoyl, and 5- to 6-membered heterocycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl;or C₆₋₁₀ aryl C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, nitro, hydroxy, amino, mono-C₁₋₆alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy,C₁₋₆ haloalkoxy, carboxy C₁₋₆ alkylcarbonylamino, carbamoyl C₁₋₆alkylcarbonylamino, C₃₋₆ cycloalkylcarbonylamino, and C₃₋₆ cycloalkylC₁₋₆ alkylamino.

[Item 29]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R2A and R2B are each independently hydrogen; alkyl; formyl; substitutedcarbonyl; alkyl substituted with one to the maximum substitutable numberof the same or different substituents selected from the group consistingof hydroxy, substituted oxy, substituted carbonyl, amino, substitutedamino, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, andsubstituted heterocycloalkyl; arylalkyl; arylalkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, nitro,hydroxy, substituted oxy, amino, substituted amino, alkyl, andsubstituted alkyl; heteroarylalkyl; or substituted heteroarylalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substituted alkyl,and substituted heteroarylalkyl in R2A and R2B each independently haveone to the maximum substitutable number of the same or differentsubstituents selected from substituent group IV, or R2A and R2B,together with the nitrogen atom to which they are attached, form anon-aryl heterocycle, wherein the non-aryl heterocycle is optionallysubstituted with one or up to the maximum substitutable number of thesame or different substituents selected from substituent group VI. [Item30B] The compound or an enantiomer thereof, or a salt thereof, or asolvate thereof according to any one of the preceding items, wherein

R2A and R2B are each independently hydrogen; alkyl; formyl;alkylcarbonyl; arylalkylcarbonyl; alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of hydroxy, trialkylsilyloxy, alkoxy,alkoxycarbonyl, alkoxycarbonylamino, cycloalkyl, carboxy, amino,amidinoamino, alkoxycarbonyl-substituted amidinoamino, carbamoyl, andheterocycloalkyl; arylalkyl; arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,monoalkylamino, dialkylamino, alkyl, haloalkyl, alkoxy,carboxyalkylcarbonylamino, carbamoylalkylcarbonylamino,cycloalkylcarbonylamino, and cycloalalkylalkylamino; heteroarylalkyl; oralkoxycarbonyl-substituted heteroarylalkyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle, wherein the non-aryl heterocycle is optionallysubstituted with one or up to the maximum substitutable number of thesame or different sub stituents selected from sub stituent group VI.

[Item 30C]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) and R_(2B) are each independently hydrogen; C₁₋₁₂ alkyl; formyl;C₁₋₆ alkylcarbonyl; C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl; C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of hydroxy,tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₁₋₆alkoxycarbonylamino, C₃₋₁₀ cycloalkyl, carboxy, amino, amidinoamino,C₁₋₆ alkoxycarbonyl-substituted amidinoamino, carbamoyl, and 5- to6-membered heterocycloalkyl; C₆₋₁₀ aryl C₁₋₁₂ alkyl; C₆₋₁₀ aryl C₁₋₁₂alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhalogen, nitro, hydroxy, amino, mono-C₁₋₆ alkylamino, di-C₁₋₆alkylamino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, carboxy C₁₋₆alkylcarbonylamino, carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino; 5- to10-membered heteroaryl C₁₋₁₂ alkyl; or C₁₋₆ alkoxycarbonyl-substituted5- to 10-membered heteroaryl C₁₋₁₂ alkyl, or R_(2A) and R_(2B), togetherwith the nitrogen atom to which they are attached, form a 5- to6-membered non-aryl heterocycle, wherein the non-aryl heterocycle isoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, nitro, hydroxy, amino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy,C₁₋₆ alkoxycarbonyl, C₃₋₆ cycloalkylcarbonylamino, and C₃₋₆ cycloalkylC₁₋₆ alkylamino.

[Item 30D]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) and R_(2B) are each independently hydrogen; C₁₋₁₂ alkyl; C₁₋₁₂alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhydroxy, tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₁₋₆alkoxycarbonylamino, C₃₋₁₀ cycloalkyl, carboxy, amino, amidinoamino,C₁₋₆ alkoxycarbonyl-substituted amidinoamino, carbamoyl, and 5- to6-membered heterocycloalkyl; C₆₋₁₀ aryl C₁₋₁₂ alkyl; C₆₋₁₀ aryl C₁₋₁₂alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhalogen, nitro, hydroxy, amino, mono-C₁₋₆ alkylamino, di-C₁₋₆alkylamino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, carboxy C₁₋₆alkylcarbonylamino, carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino; 5- to10-membered heteroaryl C₁₋₁₂ alkyl; or C₁₋₆ alkoxycarbonyl-substituted5- to 10-membered heteroaryl C₁₋₁₂ alkyl, or R_(2A) and R_(2B), togetherwith the nitrogen atom to which they are attached, form a 5- to6-membered non-aryl heterocycle, wherein the non-aryl heterocycle isoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, nitro, hydroxy, amino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy,C₁₋₆ alkoxycarbonyl, C₃₋₆ cycloalkylcarbonylamino, and C₃₋₆ cycloalkylC₁₋₆ alkylamino.

[Item 30]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is alkyl; alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of amidinoamino, carbamoyl, carboxy, hydroxy, and cycloalkyl;arylalkyl; or arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,substituted amino, and hydroxy, wherein the substituted amino has one tothe maximum substitutable number of the same or different substituentsselected from substituent group IV.

[Item 31B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, carbamoyl, carboxy, hydroxy, andC₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; or C₆₋₁₀ aryl C₁₋₆ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, substitutedamino, and hydroxy, wherein the substituted amino has one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

[Item 31]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) is hydrogen, and R_(2B) is alkyl; alkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, carbamoyl, carboxy,hydroxy, and cycloalkyl; arylalkyl; or arylalkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of halogen and alkyl.

[Item 32B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) is hydrogen, and R_(2B) is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino,carbamoyl, carboxy, hydroxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆alkyl; or C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen and C₁₋₆ alkyl.

[Item 32]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is alkyl; alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of amidinoamino, carbamoyl, carboxy, hydroxy, and cycloalkyl;or arylalkyl.

[Item 32B]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is C₁₋₁₂ alkyl; alkyl substituted with one to the maximumsubstitutable number of the same or different sub stituents selectedfrom the group consisting of amidinoamino, carbamoyl, carboxy, hydroxy,and cycloalkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; or arylalkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of alkyl and hydroxy.

[Item 32C]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is methyl, n-propyl, isobutyl, isopentyl, amidinoaminopropyl,tert-butoxycarbonyl-substituted amidinoaminopropyl, tert-butoxyethyl,tert-butoxypropyl, (tert-butoxycarbonyl)ethyl, carboxyethyl,hydroxyethyl, hydroxypropyl, aminopropyl,2-(tert-butyl-dimethylsilyloxy)ethyl, cyclopentylmethyl,cyclohexylmethyl, benzyl, phenylethyl, naphthalenylmethyl, fluorobenzyl,chlorobenzyl, dichlorobenzyl, methylbenzyl, (tert-butyl)benzyl,methoxybenzyl, ethoxybenzyl, (tert-butoxy)benzyl,(trifluoromethoxy)benzyl, (dimethylamino)benzyl, nitrobenzyl, orhydroxybenzyl.

[Item 32D]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R_(2A) and R_(2B) are each independently isopropyl, isobutyl, sec-butyl,pentyl, isopentyl, n-hexyl, heptyl, amidinoaminopropyl,tert-butoxycarbonyl-substituted amidinoaminopropyl, tert-butoxyethyl,tert-butoxycarbonylmethyl, (tert-butoxycarbonyl)ethyl, carbamoylethyl,carboxyethyl, hydroxyethyl, aminopropyl, aminobutyl,((tert-butoxycarbonyl)amino)butyl, cyclopentylmethyl, cyclohexylmethyl,(1,2,3,4-tetrahydronaphthalenyl)methyl, (tetrahydro-2H-pyranyl)methyl,benzyl, phenylethyl, naphthalenylmethyl, (naphthalenyl)ethyl,β-hydroxyphenethyl, α-(hydroxymethyl)phenethyl, fluorobenzyl,chlorobenzyl, dichlorobenzyl, (fluorophenyl)ethyl, methylbenzyl,(trifluoromethyl)benzyl, methoxybenzyl, (tert-butoxy)benzyl,hydroxybenzyl, pyridinylmethyl, quinolinylethyl,(1-(tert-butoxycarbonyl)-1H-indolyl)ethyl, cyclopentyl, or cyclohexyl,or R_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a pyrrolidine ring or piperidine ring.

[Item 32E]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is n-propyl, isobutyl, isopentyl, amidinoaminopropyl,tert-butoxycarbonyl-substituted amidinoaminopropyl,(methoxycarbonyl)ethyl, (tert-butoxycarbonyl)ethyl, carboxyethyl,hydroxyethyl, aminopropyl, (tert-butyl dim ethyl silyloxy)ethyl,((tert-butoxycarbonyl)amino)butyl, cyclopentylmethyl, cyclohexylmethyl,cyclohexylethyl, benzyl, phenylethyl, phenylpropyl, phenylbutyl,naphthalenylmethyl, naphthalenylethyl, chlorobenzyl, methylbenzyl,(methylphenyl)ethyl, (isopropylphenyl)ethyl, (tert-butoxy)benzyl, orhydroxybenzyl.

[Item 32F]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the compound is a compound selected from the group consisting ofcompound numbers IIB-1 to IIB-1129 and IIF-1 to IIF-1047.

[Item 33]

An antiviral agent for a virus in the Lyssavirus genus, comprising thecompound according to any one of the preceding items or apharmaceutically acceptable salt thereof.

[Item 34]

The antiviral agent according to any one of the preceding items, whereinthe virus in the Lyssavirus genus comprises a rabies virus.

[Item 35]

A medicament comprising the compound according to any one of thepreceding items or a pharmaceutically acceptable salt thereof.

[Item 36]

The medicament according to any one of the preceding items, which is aprophylactic agent or a therapeutic agent for rabies.

[Item 37]

A pharmaceutical composition comprising the compound according to anyone of the preceding items or a pharmaceutically acceptable saltthereof, and a pharmaceutically acceptable carrier.

[Item 38]

A pharmaceutical composition for the prophylaxis or treatment of rabies,comprising the compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable carrier.

[Item 39]

An anticancer agent comprising the compound according to any one of thepreceding items or a pharmaceutically acceptable salt thereof.

[Item 40]

The medicament according to any one of the preceding items, which is aprophylactic agent or a therapeutic agent for cancer.

[Item 41]

A pharmaceutical composition for the prophylaxis or treatment of cancer,comprising the compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable carrier.

[Item 42]

A method for the prophylaxis or treatment of rabies, characterized byadministering a prophylactically or therapeutically effective amount ofthe compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, the antiviral agent accordingto any one of the preceding items, the medicament according to any oneof the preceding items, or the pharmaceutical composition according toany one of the preceding items to a patient in need thereof.

[Item 43]

Use of the compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, or the antiviral agentaccording to any one of the preceding items, for the manufacture of amedicament for the prophylaxis or treatment of rabies.

[Item 44]

A method for the prophylaxis or treatment of cancer, characterized byadministering a prophylactically or therapeutically effective amount ofthe compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, the anticancer agent accordingto any one of the preceding items, the medicament according to any oneof the preceding items, or the pharmaceutical composition according toany one of the preceding items to a patient in need thereof.

[Item 45]

Use of the compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, or the anticancer agentaccording to any one of the preceding items, for the manufacture of amedicament for the prophylaxis or treatment of cancer.

[Item 46]

A method for the prophylaxis or treatment of rabies, comprisingadministering an effective amount of the compound according to any oneof the preceding items or a pharmaceutically acceptable salt thereof toa subject in need thereof.

[Item 47]

A method for the prophylaxis or treatment of cancer, comprisingadministering an effective amount of the compound according to any oneof the preceding items or a pharmaceutically acceptable salt thereof toa subject in need thereof.

The present disclosure also provides the following items.

[Item A1]

A compound represented by formula IF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, optionally substituted cycloalkylalkyl, or optionallysubstituted heterocycloalkylalkyl, and

R₄ is hydrogen, optionally substituted alkyl, optionally substitutedalkenyl, optionally substituted alkynyl, optionally substitutedarylalkyl, optionally substituted heteroarylalkyl, optionallysubstituted cycloalkylalkyl, optionally substitutedheterocycloalkylalkyl, optionally substituted alkylcarbonyl, optionallysubstituted alkoxycarbonyl, optionally substituted arylcarbonyl,optionally substituted heteroarylcarbonyl, or optionally substitutedcarbamoyl.

[Item A2]

A compound represented by formula IB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, optionally substituted cycloalkylalkyl, or optionallysubstituted heterocycloalkylalkyl, and

R₄ is hydrogen, optionally substituted alkyl, optionally substitutedalkenyl, optionally substituted alkynyl, optionally substitutedarylalkyl, optionally substituted heteroarylalkyl, optionallysubstituted cycloalkylalkyl, optionally substitutedheterocycloalkylalkyl, optionally substituted alkylcarbonyl, optionallysubstituted alkoxycarbonyl, optionally substituted arylcarbonyl,optionally substituted heteroarylcarbonyl, or optionally substitutedcarbamoyl.

[Item A3]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, or optionally substituted cycloalkylalkyl, and

R₄ is hydrogen, optionally substituted alkyl, optionally substitutedalkylcarbonyl, optionally substituted arylcarbonyl, optionallysubstituted alkoxycarbonyl, or optionally substituted carbamoyl.

[Item A3a]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, or optionally substituted cycloalkylalkyl, and

R₄ is hydrogen, optionally substituted alkyl, optionally substitutedalkylcarbonyl, optionally substituted arylcarbonyl, or optionallysubstituted alkoxycarbonyl.

[Item A4]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted C₁₋₆ alkyl,optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl, optionally substituted 5-to 10-membered heteroaryl C₁₋₆ alkyl, or optionally substituted C₃₋₆cycloalkyl C₁₋₆ alkyl, and

R₄ is hydrogen, optionally substituted C₁₋₆ alkyl, optionallysubstituted C₁₋₆ alkylcarbonyl, optionally substituted C₆₋₁₀arylcarbonyl, optionally substituted C₁₋₆ alkoxycarbonyl, or optionallysubstituted C₁₋₆ alkylcarbamoyl.

[Item A4b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted C₁₋₆ alkyl,optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl, optionally substituted 5-to 10-membered heteroaryl C₁₋₆ alkyl, or optionally substituted C₃₋₆cycloalkyl C₁₋₆ alkyl, and

R₄ is hydrogen, optionally substituted C₁₋₆ alkyl, optionallysubstituted C₁₋₆ alkylcarbonyl, optionally substituted C₆₋₁₀arylcarbonyl, or optionally substituted C₁₋₆ alkoxycarbonyl.

[Item A5]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently C₁₋₆ alkyl, hydroxy-substitutedC₁₋₆ alkyl, carbamoyl-substituted C₁₋₆ alkyl, amino-substituted C₁₋₆alkyl, amidinoamino-substituted C₁₋₆ alkyl, carboxy-substituted C₁₋₆alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted 5- to10-membered heteroaryl C₁₋₆ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ arylC₁₋₆ alkyl, hydroxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl,halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₆ alkyl, (optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆ alkyl,C₁₋₄ alkoxycarbonyl-substituted C₁₋₆ alkyl, C₁₋₄ alkoxycarbonylamino-substituted C₁₋₆ alkyl, 5- to 6-membered heterocycloalkyl- substituted C₁₋₆alkyl, or C₃₋₆ cycloalkyl C₁₋₆ alkyl.

[Item A5a]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently C₁₋₆ alkyl, hydroxy-substitutedC₁₋₆ alkyl, carbamoyl-substituted C₁₋₆ alkyl, amino-substituted C₁₋₆alkyl, amidinoamino-substituted C₁₋₆ alkyl, carboxy-substituted C₁₋₆alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted 5- to10-membered heteroaryl C₁₋₆ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ arylC₁₋₆ alkyl, hydroxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl,halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted C₁₋₆ alkyl, C₁₋₄alkoxycarbonylamino-substituted C₁₋₆ alkyl, 5- to 6-memberedheterocycloalkyl-substituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl C₁₋₆ alkyl.

[Item A5b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, optionally substituted C₁₋₆ alkyl, optionallysubstituted C₁₋₆ alkylcarbonyl, optionally substituted C₆₋₁₀ aryl C₁₋₆alkylcarbonyl, optionally substituted C₆₋₁₀ arylcarbonyl, optionallysubstituted C₁₋₆ alkoxycarbonyl, optionally substituted C₆₋₁₀ aryl C₁₋₆alkoxycarbonyl, carbamoyl, optionally substituted C₁₋₆ alkylcarbamoyl,or optionally substituted C₆₋₁₀ aryl C₁₋₆ alkylcarbamoyl.

[Item A5c]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl oroptionally substituted arylalkyl.

[Item A5d]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted C₁₋₆ alkylor optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl.

[Item A5e]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl,C₁₋₄ alkyl-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, halogen-substituted C₆₋₁₀aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, or(optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆ alkyl.

[Item A5f]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is naphthalen-1-ylmethyl or optionally substituted benzyl.

[Item A5g]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently alkyl or optionally substituted benzyl,and R₂ is optionally substituted benzyl.

[Item A5h]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently C₁₋₆ alkyl, benzyl, C₁₋₄alkyl-substituted benzyl, chloro-substituted benzyl, C₁₋₄alkoxy-substituted benzyl, or amino-substituted benzyl, and R₂ is benzylor chloro-substituted benzyl.

[Item A5i]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ and R₃ are each independently isobutyl, isopentyl,4-(dimethylamino)benzyl, 4-methylbenzyl, 4-methoxybenzyl,3-chlorobenzyl, 4-chlorobenzyl, or 3,4-dichlorobenzyl, and R₂ is benzyl,3-chlorobenzyl, or 3,4-dichlorobenzyl.

[Item A6]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₆₋₁₀ arylcarbonyl,C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, C₆₋₁₀ aryl C₁₋₆alkoxycarbonyl, carbamoyl, C₁₋₆ alkylcarbamoyl, or C₆₋₁₀ aryl C₁₋₆alkylcarbamoyl.

[Item A6b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₆₋₁₀ arylcarbonyl, orC₁₋₆ alkoxycarbonyl.

[Item A7]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, C₁₋₄ alkyl, C₁₋₄ alkylcarbonyl, C₆ arylcarbonyl, C₆ arylC₁₋₄ alkylcarbonyl, C₁₋₄ alkoxycarbonyl, C₆ aryl C₁₋₄ alkoxycarbonyl,carbamoyl, C₁₋₄ alkylcarbamoyl, or C₆ aryl C₁₋₄ alkylcarbamoyl.

[Item A1b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, C₁₋₄ alkyl, C₁₋₄ alkylcarbonyl, C₆ arylcarbonyl, or C₁₋₄alkoxycarbonyl.

[Item A8]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, methyl, ethyl, acetyl, benzoyl, methoxycarbonyl,tert-butoxycarbonyl, or propylcarbamoyl.

[Item A8b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen, methyl, ethyl, acetyl, benzoyl, methoxycarbonyl, ortert-butoxycarbonyl.

[Item A9]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is C₁₋₄ alkyl, hydroxy-substituted C₁₋₄ alkyl, carbamoyl-substitutedC₁₋₄ alkyl, amino-substituted C₁₋₄ alkyl, amidinoamino-substituted C₁₋₄alkyl, carboxy-substituted C₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxycarbonyl-substituted 5- to 10-membered heteroaryl C₁₋₄ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₄ alkyl, halogen-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxycarbonyl-substituted C₁₋₄ alkyl, C₁₋₄alkoxycarbonylamino-substituted C₁₋₄ alkyl, 5- to 6-memberedheterocycloalkyl-substituted C₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

[Item A9b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isopropyl, 1-methylpropyl, isobutyl, isopentyl, n-hexyl,hydroxymethyl, 2-hydroxyethyl, carbamoylmethyl, 3-amino-3-oxopropyl,4-aminobutyl, 3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 2-(naphthalen-1-yl)ethyl,2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 4-fluorobenzyl, 3-chlorobenzyl,4-chlorobenzyl, 3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl,2-(tert-butoxy)-2-oxoethyl, 4-((tert-butoxycarbonyl)amino)butyl,(tetrahydro-2H-pyran-2-yl)methyl, or cyclohexylmethyl.

[Item A10]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isobutyl, 2-hydroxyethyl, 3-amino-3-oxopropyl, 4-aminobutyl,2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,2-(naphthalen-1-yl)ethyl,2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 3-chlorobenzyl, 4-chlorobenzyl,3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl, 2-(tert-butoxy)-2-oxoethyl,4-((tert-butoxycarbonyl)amino)butyl, (tetrahydro-2H-pyran-2-yl)methyl,or cyclohexylmethyl.

[Item A10b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is 1-methylpropyl, isopropyl, isobutyl, isopentyl, n-hexyl, benzyl,4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl, carbamoylmethyl,carbamoylethyl, 3-(amidinoamino)propyl, hydroxymethyl, 2-hydroxyethyl,phenethyl, naphthalen-1-ylmethyl, or cyclohexylmethyl.

[Item A11]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isopropyl, isobutyl, isopentyl, benzyl, 4-hydroxybenzyl,4-fluorobenzyl, 2-carboxyethyl, carbamoylmethyl, 3-(amidinoamino)propyl,2-hydroxyethyl, phenethyl, naphthalen-1-ylmethyl, or n-hexyl.

[Item A11b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is 1-methylpropyl, isopropyl, isobutyl, benzyl, 4-hydroxybenzyl,2-carboxyethyl, 3-(amidinoamino)propyl, or naphthalen-1-ylmethyl.

[Item A12]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₆ alkyl, hydroxy-substituted C₁₋₄ alkyl, carbamoyl-substitutedC₁₋₄ alkyl, amino-substituted C₁₋₆ alkyl, amidinoamino-substituted C₁₋₄alkyl, carboxy-substituted C₁₋₄ alkyl, C₁₋₄ alkoxycarbonyl-substitutedC₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ aryl C₁₋₄alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, halo-substitutedC₆₋₁₀ aryl C₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

[Item A12b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is methyl, isopropyl, isobutyl, isopentyl, n-hexyl,3-amino-3-oxopropyl, 3-(tert-butoxy)-3-oxopropyl, benzyl,naphthalen-1-ylmethyl, 2-carboxyethyl, carbamoylmethyl,3-(amidinoamino)propyl, 4-fluorobenzyl, 4-hydroxybenzyl,4-(tert-butoxy)benzyl, 3,4-dichlorobenzyl, naphthalen-1-ylmethyl,phenethyl, hydroxymethyl, 2-hydroxyethyl, or cyclohexylmethyl.

[Item A13]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is methyl, isobutyl, isopentyl, 3-(tert-butoxy)-3-oxopropyl, benzyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-(tert-butoxy)benzyl,3,4-dichlorobenzyl, or cyclohexylmethyl.

[Item A14]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isopropyl, isobutyl, isopentyl, n-hexyl, cyclohexylmethyl, benzyl,phenethyl, naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl,2-carboxyethyl, carbamoylmethyl, carbamoylethyl, 3 -(amidinoamino)propyl, hydroxymethyl, or hydroxyethyl.

[Item A14b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, isopentyl, cyclohexylmethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl,carbamoylmethyl, 3-(amidinoamino)propyl, or hydroxyethyl.

[Item A14c]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, benzyl, 4-hydroxybenzyl, 2-carboxyethyl,3-(amidinoamino)propyl, or naphthalen-1-ylmethyl.

[Item A15]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is C₁₋₄ alkyl, hydroxy-substituted C₁₋₄ alkyl, carbamoyl-substitutedC₁₋₄ alkyl, C₁₋₄ alkoxycarbonyl-substituted C₁₋₄ alkyl,amino-substituted C₁₋₄ alkyl, amidinoamino-substituted C₁₋₄ alkyl,carboxy-substituted C₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

[Item A15b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, which is isopropyl,isobutyl, isopentyl, n-hexyl, hydroxymethyl, 2-hydroxyethyl,carbamoylmethyl, 3-amino-3-oxopropyl, 4-aminobutyl,3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl, 3-methylbenzyl,4-methylbenzyl, 3-methoxy-3-oxopropyl,4-((tert-butoxycarbonyl)amino)butyl, or cyclohexylmethyl.

[Item A16]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isobutyl, isopentyl, 3-amino-3-oxopropyl, 3-methoxy-3-oxopropyl,4-aminobutyl, 2-carboxyethyl, benzyl, phenethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 4-((tert-butoxycarbonyl)amino)butyl, orcyclohexylmethyl.

[Item A17]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isopropyl, isobutyl, isopentyl, n-hexyl, cyclohexylmethyl, benzyl,phenethyl, naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl,2-carboxyethyl, carbamoylmethyl, carbamoylethyl, 3-(amidinoamino)propyl, hydroxymethyl, or hydroxyethyl.

[Item A17b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isobutyl, isopentyl, benzyl, phenethyl, 4-hydroxybenzyl,2-carboxyethyl, carbamoylmethyl, 3-(amidinoamino)propyl, hydroxymethyl,or naphthalen-1-ylmethyl.

[Item A17c]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isobutyl, benzyl, 4-hydroxybenzyl, 2-carboxyethyl,3-(amidinoamino)propyl, or naphthalen-1-ylmethyl.

[Item A18]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen or alkyl.

[Item A18a]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen or C₁₋₆ alkyl.

[Item A18b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen or ethyl.

[Item A19]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₄ is hydrogen.

[Item A20]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein R₁ is C₁₋₆alkyl or C₆₋₁₀ aryl C₁₋₆ alkyl, and R₂ and R₃ are each independentlyC₁₋₆ alkyl or optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl.

[Item A21]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, isopentyl, or benzyl, R₂ is isobutyl, benzyl, phenethyl,3-methylbenzyl, 4-methylbenzyl, or 3,4-dichlorobenzyl, and R₃ isisobutyl, benzyl, phenethyl, 3-methylbenzyl, or 4-methylbenzyl.

[Item A22]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the compound is a compound of formula IF, R₁ is isobutyl, R₂ is benzyl,and R₃ is benzyl.

[Item A23]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the compound is compound of formula IF, R₁ is benzyl, R₂ is benzyl, andR₃ is isobutyl.

[Item A24]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the compound is a compound of formula IF, R₁ is isobutyl, R₂ is benzyl,and R₃ is 3-methylbenzyl.

[Item A25]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

the compound is a compound of formula IF, R₁ is benzyl, R₂ is3,4-dichlorobenzyl, and R₃ is isobutyl.

[Item A26]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein thecompound of formula IF is a compound selected from the group consistingof IF-1, IF-2, IF-3, IF-4, IF-5, IF-6, IF-7, IF-8, IF-9, IF-10, IF-11,IF-12, IF-13, IF-14, IF-15, IF-16, IF-17, IF-18, IF-19, IF-20, IF-22,IF-23, IF-24, IF-25, IF-26, IF-27, IF-28, IF-29, IF-30, IF-31, IF-32,IF-33, IF-34, IF-35, IF-36, IF-38, IF-39, IF-40, IF-41, IF-42, IF-43,IF-44, IF-45, IF-46, IF-47, IF-49, IF-50, IF-54, IF-57, IF-58, IF-68,IF-69, IF-70, IF-71, IF-72, IF-73, IF-74, IF-76, IF-77, IF-80, and IF-81to IF-884.

[Item A26b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein thecompound of formula IF is(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-1,7-dibenzyl-N-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-N,1-dibenzyl-7-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isopentyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-phenethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3-methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(4-methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(3-methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,(3S*,3aS*,6S*,7R*,7aS*)-1-benzyl-N-(3,4-dichlorobenzyl)-7-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide,or(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-4-ethyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-caboxamide.

[Item A27]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein thecompound of formula IB is a compound selected from the group consistingof D3-1, IB-2, IB-3, IB-4, IB-5, IB-6, IB-7, IB-8, IB-9, D3-10, D3-11,IB-12, IB-13, IB-14, IB-15, IB-16, IB-17, IB-18, IB-19, IB-20, IB-21,IB-22, IB-23, IB-24, IB-25, IB-26, IB-27, IB-28, IB-29, IB-30, IB-31,IB-32, IB-33, IB-34, IB-35, IB-36, IB-37, IB-38, IB-39, IB-40, IB-41,IB-42, IB-43, IB-44, IB-45, IB-46, IB-47, IB-49, IB-50, IB-54, IB-57,IB-58, IB-64, IB-68, IB-69, IB-70, IB-71, IB-72, IB-73, IB-74, IB-75,IB-76, IB-77, IB-78, IB-79, IB-80, and IB-81 to IB-923.

[Item A27b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein thecompound of formula IB is(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N,1-diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide,(3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-N,7-diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide,(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1,7-diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide,(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isopentyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide,(3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-7-isobutyl-N-phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide,(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3-methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide,or(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(3-methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-caboxamide.

[Item A28]

A compound represented by formula IIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, optionally substituted cycloalkylalkyl, or optionallysubstituted heterocycloalkylalkyl.

[Item A29]

A compound represented by formula IIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, optionally substituted cycloalkylalkyl, or optionallysubstituted heterocycloalkylalkyl.

[Item A30]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, or optionally substituted cycloalkylalkyl.

[Item A31]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted C₁₋₆ alkyl,optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl, optionally substituted 5-to 10-membered heteroaryl C₁₋₆ alkyl, or optionally substituted C₃₋₆cycloalkyl C₁₋₆ alkyl.

[Item A32]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently C₁₋₆ alkyl, hydroxy-substitutedC₁₋₆ alkyl, carbamoyl-substituted C₁₋₆ alkyl, amino-substituted C₁₋₆alkyl, amidinoamino-substituted C₁₋₆ alkyl, carboxy-substituted C₁₋₆alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted 5- to10-membered heteroaryl C₁₋₆ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ arylC₁₋₆ alkyl, hydroxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl,halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₆ alkyl, (optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆ alkyl,C₁₋₄ alkoxycarbonyl-substituted C₁₋₆ alkyl, C₁₋₄ alkoxycarbonylamino-substituted C₁₋₆ alkyl, 5- to 6-membered heterocycloalkyl-substituted C₁₋₆alkyl, or C₃₋₆ cycloalkyl C₁₋₆ alkyl.

[Item A32a]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently C₁₋₆ alkyl, hydroxy-substitutedC₁₋₆ alkyl, carbamoyl-substituted C₁₋₆ alkyl, amino-substituted C₁₋₆alkyl, amidinoamino-substituted C₁₋₆ alkyl, carboxy-substituted C₁₋₆alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted 5- to10-membered heteroaryl C₁₋₆ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ arylC₁₋₆ alkyl, hydroxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl,halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-sub stituted C₁₋₆ alkyl, C₁₋₄alkoxycarbonylamino-sub stituted C₁₋₆ alkyl, 5- to 6-memberedheterocycloalkyl-sub stituted C₁₋₆ alkyl, or C₃₋₆ cycloalkylC₁₋₆alkyl.

[Item A32b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted alkyl oroptionally substituted arylalkyl.

[Item A32c]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂ and R₃ are each independently optionally substituted C₁₋₆ alkylor optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl.

[Item A33]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is C₁₋₄ alkyl, hydroxy-substituted C₁₋₄ alkyl, carbamoyl-substitutedC₁₋₄ alkyl, amino-substituted C₁₋₄ alkyl, amidinoamino-sub stituted C₁₋₄alkyl, carboxy-substituted C₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxycarbonyl-substituted 5- to 10-membered heteroaryl C₁₋₄ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₄ alkyl, halogen-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxycarbonyl-substituted C₁₋₄ alkyl, C₁₋₄alkoxycarbonylamino-substituted C₁₋₄ alkyl, 5- to 6-memberedheterocycloalkyl-substituted C₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

[Item A33b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isopropyl, 1-methylpropyl, isobutyl, isopentyl, n-hexyl,hydroxymethyl, 2hydroxyethyl, carbamoylmethyl, 3-amino-3-oxopropyl,4-aminobutyl, 3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 2-(naphthalen-1-yl)ethyl,2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 4-fluorobenzyl, 3-chlorobenzyl,4-chlorobenzyl, 3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl,2-(tert-butoxy)-2-oxoethyl, 3-(tert-butoxy)-3-oxopropyl,4-((tert-butoxycarbonyl)amino)butyl, (tetrahydro-2H-pyran-2-yl)methyl,cyclohexylmethyl, or

[Item A34]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isobutyl, 2-hydroxyethyl, 3-amino-3-oxopropyl, 4-aminobutyl,2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,2-(naphthalen-1-yl)ethyl,2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 3-chlorobenzyl, 4-chlorobenzyl,3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl, 2-(tert-butoxy)-2-oxoethyl,4-((tert-butoxycarbonyl)amino)butyl, (tetrahydro-2H-pyran-2-yl)methyl,or cyclohexylmethyl.

[Item A35]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isopropyl, isobutyl, isopentyl, benzyl, 4-hydroxybenzyl,4-fluorobenzyl, 2-carboxyethyl, carbamoylmethyl, 3-(amidinoamino)propyl,hydroxyethyl, phenethyl, naphthalen-1-ylmethyl, or n-hexyl.

[Item A35b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₂ is isopropyl, 1-methylpropyl, isobutyl, 3-(amidinoamino)propyl,2-carboxyethyl, benzyl, naphthalen-1-ylmethyl, 4-hydroxybenzyl,4-(tert-butoxy)benzyl, 3-(tert-butoxy)-3-oxopropyl, or

[Item A36]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₆ alkyl, hydroxy-substituted C₁₋₄ alkyl, carbamoyl-substitutedC₁₋₄ alkyl, amino-substituted C₁₋₆ alkyl, amidinoamino-sub stituted C₁₋₄alkyl, carboxy-substituted C₁₋₄ alkyl, C₁₋₄ alkoxycarbonyl-substitutedC₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ aryl C₁₋₄alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, halo-substitutedC₆₋₁₀ aryl C₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

[Item A36b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is methyl, isopropyl, isobutyl, isopentyl, n-hexyl, 2-hydroxyethyl,carbamoylmethyl, 3-amino-3-oxopropyl, 3-(amidinoamino)propyl,2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,4-hydroxybenzyl, 4-fluorobenzyl, 3,4-dichlorobenzyl,4-(tert-butoxy)benzyl, 3-(tert-butoxy)-3 -oxopropyl, hydroxymethyl,cyclohexylmethyl, or

[Item A37]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is methyl, isobutyl, isopentyl, 3-(tert-butoxy)-3-oxopropyl, benzyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-(tert-butoxy)benzyl,3,4-dichlorobenzyl, or cyclohexylmethyl.

[Item A38]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, isopentyl, cyclohexylmethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl,carbamoylmethyl, 3-(amidinoamino)propyl, or hydroxyethyl.

[Item A38b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, 3-(amidinoamino)propyl, 2-carboxyethyl, benzyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-(tert-butoxy)benzyl,3-(tert-butoxy)-3-oxopropyl, or

[Item A39]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is C₁₋₄ alkyl, hydroxy-substituted C₁₋₄ alkyl, carbamoyl-substitutedC₁₋₄ alkyl, C₁₋₄ alkoxycarbonyl-sub stituted C₁₋₄ alkyl,amino-substituted C₁₋₄ alkyl, amidinoamino-substituted C₁₋₄ alkyl,carboxy-substituted C₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

[Item A39b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isopropyl, isobutyl, isopentyl, n-hexyl, hydroxymethyl,2-hydroxyethyl, carbamoylmethyl, 3-amino-3-oxopropyl, 4-aminobutyl,3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 3-methylbenzyl, 4-methylbenzyl, 4-hydroxybenzyl,4-fluorobenzyl, 4-(tert-butoxy)benzyl, 3-methoxy-3-oxopropyl,3-(tert-butoxy)-3-oxopropyl, 4-((tert-butoxycarbonyl)amino)butyl,cyclohexylmethyl, or

[Item A40]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isobutyl, isopentyl, 3-amino-3-oxopropyl, 3-methoxy-3-oxopropyl,4-aminobutyl, 2-carboxyethyl, benzyl, phenethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 4-((tert-butoxycarbonyl)amino)butyl, orcyclohexylmethyl.

[Item A41]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isobutyl, isopentyl, benzyl, phenethyl, 4-hydroxybenzyl,2-carboxyethyl, carbamoylmethyl, 3-(amidinoamino)propyl, hydroxymethyl,or naphthalen-1-ylmethyl.

[Item A41b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₃ is isobutyl, 2-carboxyethyl, 3-(amidinoamino)propyl, benzyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-(tert-butoxy)benzyl,3-(tert-butoxy)-3-oxopropyl, or

[Item A42]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₆ alkyl or C₆₋₁₀ aryl C₁₋₆ alkyl, R₂ and R₃ are eachindependently C₁₋₆ alkyl or optionally substituted C₆₋₁₀ aryl C₁₋₆alkyl.

[Item A42b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂, and R₃ are each independently C₁₋₆ alkyl or optionallysubstituted C₆₋₁₀ aryl C₁₋₆ alkyl.

[Item A42c]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁, R₂, and R₃ are each independently C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl,C₁₋₄ alkyl-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, halogen-substituted C₆₋₁₀aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, or(optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆ alkyl.

[Item A42d]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is C₁₋₆ alkyl or C₆ aryl C₁₋₄ alkyl, R₂ is C₁₋₆ alkyl or C₁₋₄alkyl-substituted benzyl, and R₃ is C₁₋₆ alkyl or C₆ aryl C₁₋₄ alkyl.

[Item A43]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, benzyl, 4-(dimethylamino)benzyl, 4-methylbenzyl,4-tert-butylbenzyl, 4-methoxybenzyl, 3-chlorobenzyl, 4-chlorobenzyl, or3,4-dichlorobenzyl, R₂ is isobutyl, benzyl, naphthalen-1-ylmethyl,4-methylbenzyl, 4-chlorobenzyl, or 3,4-dichlorobenzyl, and R₃ isisobutyl, isopentyl, or benzyl.

[Item A43b]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein

R₁ is isobutyl, isopentyl, or benzyl, R₂ is isobutyl, benzyl, phenethyl,3-methylbenzyl, 4-methylbenzyl, or 3,4-dichlorobenzyl, and R₃ isisobutyl, benzyl, phenethyl, 3-methylbenzyl, or 4-methylbenzyl.

[Item A44]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein thecompound is a compound of formula IIF, R₁ is isobutyl, R₂ is4-methylbenzyl, and R₃ is benzyl.

[Item A45]

The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to any one of the preceding items, wherein thecompound is a compound of formula IIB, R₁ is benzyl, R₂ is isobutyl, andR₃ is isobutyl.

[Item A46]

An antiviral agent for a virus in the Lyssavirus genus, comprising thecompound according to any one of the preceding items or apharmaceutically acceptable salt thereof.

[Item A47]

The antiviral agent according to any one of the preceding items, whereinthe virus in the Lyssavirus genus comprises a rabies virus.

[Item A48]

A medicament comprising the compound according to any one of thepreceding items or a pharmaceutically acceptable salt thereof, or theantiviral agent according to any one of the preceding items.

[Item A49]

The medicament according to any one of the preceding items, which is aprophylactic agent or a therapeutic agent for rabies.

[Item A50]

A pharmaceutical composition comprising the compound according to anyone of the preceding items or a pharmaceutically acceptable saltthereof, or the antiviral agent according to any one of the precedingitems, and a pharmaceutically acceptable carrier.

[Item A51]

A pharmaceutical composition for the prophylaxis or treatment of rabies,comprising the compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, or the antiviral agentaccording to any one of the preceding items, and a pharmaceuticallyacceptable carrier.

[Item A52]

The compound according to any one of the preceding items or apharmaceutically acceptable salt thereof for use as an antiviral agentfor a virus in the Lyssavirus genus, preferably a rabies virus, or forthe prophylaxis or treatment of rabies.

[Item A53]

A method for the prophylaxis or treatment of rabies, characterized byadministering a prophylactically or therapeutically effective amount ofthe compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, the antiviral agent accordingto any one of the preceding items, the medicament according to any oneof the preceding items, or the pharmaceutical composition according toany one of the preceding items to a patient in need thereof

[Item A54]

Use of the compound according to any one of the preceding items or apharmaceutically acceptable salt thereof, or the antiviral agentaccording to any one of the preceding items, for the manufacture of amedicament for the prophylaxis or treatment of rabies.

The present disclosure is intended so that one or more of the featuresdescribed above can be provided not only as the explicitly disclosedcombinations, but also as other combinations thereof. Additionalembodiments and advantages of the present disclosure are recognized bythose skilled in the art by reading and understanding the followingdetailed description as needed.

Advantageous Effects of Invention

The compounds of the present disclosure exhibit an excellent antiviralaction on viruses in the Lyssavirus genus including the rabies virus.Therefore, the compounds of the present disclosure are useful as atherapeutic agent and/or prophylactic agent for rabies.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 shows an ORTEP diagram for the results of X-ray crystallographyin Synthesis Example: IF-1.

FIG. 2 shows a chromatogram upon separation of the racemate in SynthesisExample: IF-1 using a chiral column, CHIRALPAK IG (5 μm, 4.6×150 mm),mobile phase: methanol:diethylamine (100:0.1).

FIG. 3 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 4 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 5 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 6 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 7 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 8 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 9 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 10 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 11 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 12 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 13 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 14 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 15 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 16 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 17 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 18 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 19 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 20 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 21 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 22 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 23 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 24 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 25 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 26 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 27 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 28 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 29 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 30 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 31 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 32 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 33 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 34 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 35 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 36 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 37 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 38 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 39 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 40 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 41 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 42 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 43 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 44 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 45 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 46 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 47 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 48 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 49 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 50 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 51 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 52 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 53 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 54 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 55 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 56 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 57 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 58 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 59 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 60 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 61 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 62 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 63 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 64 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 65 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 66 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 67 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 68 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 69 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 70 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 71 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 72 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 73 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 74 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 75 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 76 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 77 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 78 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 79 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 80 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

FIG. 81 shows the ¹H-NMR chart for an exemplary compound of the presentdisclosure (formula in the figure).

DESCRIPTION OF EMBODIMENTS

Hereinafter, the present disclosure is described in more detail.

Throughout the entire specification, a singular expression should beunderstood as encompassing the concept thereof in the plural form,unless specifically noted otherwise. Thus, singular articles (e.g., “a”,“an”, “the”, and the like in the case of English) should also beunderstood as encompassing the concept thereof in the plural form,unless specifically noted otherwise. The terms used herein should alsobe understood as being used in the meaning that is commonly used in theart, unless specifically noted otherwise. Thus, unless definedotherwise, all terminologies and scientific technical terms that areused herein have the same meaning as the general understanding of thoseskilled in the art to which the present disclosure pertains. In case ofa contradiction, the present specification (including the definitions)takes precedence.

(Definitions)

The terms and the general technology used in the present disclosure arefirst described.

As used herein, the term “group” refers to a monovalent group, unlessespecially noted otherwise. Examples of a group that is not a monovalentgroup include alkylene group (divalent) and the like. The term “group”may also be abbreviated in the following description of substituents orthe like.

As used herein, the number of substituents when a group is defined as“optionally substituted” or “substituted” is not particularly limited aslong as it is substitutable and is one or more. The description for eachgroup is also applicable when the substituent is a part of or asubstituent on another substituent, unless specifically noted otherwise.

As used herein, “maximum substitutable number” is the maximum number ofsubstituents that a group can have. The number can vary for each group.For example, the number is 3 for a methyl group, 5 for an ethyl group, 7for a benzyl group, and 10 for a naphthalenyl ethyl group.

For a group that is modified by “optionally substituted” or“substituted” herein, any portion of the group can be substituted. Forexample, “optionally substituted arylalkyl” and “substituted arylalkyl”can have the aryl moiety substituted, the alkyl moiety substituted, orboth the aryl moiety and the alkyl moiety substituted.

As used herein, the substituent used when “optionally substituted” canbe one or more of the same or different substituents selected from anyone of the following substituent groups Ito VI. While the types of atomswithin a substituent associated with attachment are not particularlylimited by the type of substituent, if the atom to which a substituentattaches is an oxygen atom, a nitrogen atom, or a sulfur atom, the atomis limited to and selected from those with an attachment point in thefollowing substituents that is a carbon atom.

Substituent group I consists of halogen, hydroxy, oxo, carboxy, amino,imino, hydroxyamino, hydroxyimino, formyl, formyloxy, carbamoyl,sulfamoyl, sulfanyl, sulfino, sulfo, thioformyl, thiocarboxy,dithiocarboxy, thiocarbamoyl, cyano, nitro, nitroso, azide, hydrazino,ureide, amidino, amidinoamino, unsubstituted or substituted alkyl,unsubstituted or substituted alkenyl, unsubstituted or substitutedalkynyl, unsubstituted or substituted aryl, unsubstituted or substitutedcycloalkyl, unsubstituted or substituted heteroaryl, unsubstituted orsubstituted heterocycloalkyl, unsubstituted or substituted alkyloxy,unsubstituted or substituted alkenyloxy, unsubstituted or substitutedalkynyloxy, unsubstituted or substituted aryl-Lx-oxy, unsubstituted orsubstituted cycloalkyl-Lx-oxy, unsubstituted or substitutedheteroaryl-Lx-oxy, unsubstituted or substituted heterocycloalkyl-Lx-oxy,unsubstituted or substituted alkyloxyalkyl, unsubstituted or substitutedalkenyloxyalkyl, unsubstituted or substituted alkynyloxyalkyl,unsubstituted or substituted aryloxyalkyl, unsubstituted or substitutedcycloalkyloxyalkyl, unsubstituted or substituted heteroaryloxyalkyl,unsubstituted or substituted heterocycloalkyloxyalkyl, unsubstituted orsubstituted alkyloxyalkyloxy, unsubstituted or substitutedalkenyloxyalkyloxy, unsubstituted or substituted alkynyloxyalkyloxy,unsubstituted or substituted aryloxyalkyloxy, unsubstituted orsubstituted cy,cloalkyloxyalkyloxy, unsubstituted or substitutedheteroaryloxyalkyloxy, unsubstituted or substitutedheterocy,cloalkyloxyalkyloxy, unsubstituted or substitutedalkylcarbonyl, unsubstituted or substituted alkenylcarbonyl,unsubstituted or substituted alkynylcarbonyl, unsubstituted orsubstituted aryl-Lx-carbonyl, unsubstituted or substitutedcycloalkyl-Lx-carbonyl, unsubstituted or substitutedheteroaryl-Lx-carbonyl, unsubstituted or substitutedheterocycloalkyl-Lx-carbonyl, unsubstituted or substitutedalkylcarbonyloxy, unsubstituted or substituted alkenylcarbonyloxy,unsubstituted or substituted alkynylcarbonyloxy, unsubstituted orsubstituted aryl-Lx-carbonyloxy, unsubstituted or substitutedcy,cloalkyl-Lx-carbonyloxy, unsubstituted or substitutedheteroaryl-Lx-carbonyloxy, unsubstituted or substitutedheterocycloalkyl-Lx-carbonyloxy, unsubstituted or substitutedalkylcarbonylamino, unsubstituted or substituted alkenylcarbonylamino,unsubstituted or substituted alkynylcarbonylamino, unsubstituted orsubstituted aryl-Lx-carbonylamino, unsubstituted or substitutedcycloalkyl-Lx-carbonylamino, unsubstituted or substitutedheteroaryl-Lx-carbonylamino, unsubstituted or substitutedheterocycloalkyl-Lx-carbonylamino, unsubstituted or substitutedalkylcarbonylthio, unsubstituted or substituted alkenylcarbonylthio,unsubstituted or substituted alkynylcarbonylthio, unsubstituted orsubstituted aryl-Lx-carbonylthio, unsubstituted or substitutedcycloalkyl-Lx-carbonylthio, unsubstituted or substitutedheteroaryl-Lx-carbonylthio, unsubstituted or substitutedheterocycloalkyl-Lx-carbonylthio, unsubstituted or substitutedalkylcarbonylimino, unsubstituted or substituted alkenylcarbonylimino,unsubstituted or substituted alkynylcarbonylimino, unsubstituted orsubstituted aryl-Lx-carbonylimino, unsubstituted or substitutedcycloalkyl-Lx-carbonylimino, unsubstituted or substitutedheteroaryl-Lx-carbonylimino, unsubstituted or substitutedheterocycloalkyl-Lx-carbonylimino, unsubstituted or substitutedalkylthio, unsubstituted or substituted alkenylthio, unsubstituted orsubstituted alkynylthio, unsubstituted or substituted aryl-Lx-thio,unsubstituted or substituted cycloalkyl-Lx-thio, unsubstituted orsubstituted heteroaryl-Lx-thio, unsubstituted or substitutedheterocycloalkyl-Lx-thio, unsubstituted or substituted alkylamino,unsubstituted or substituted alkenylamino, unsubstituted or substitutedalkynylamino, unsubstituted or substituted alkynylamino, unsubstitutedor substituted aryl-Lx-amino, unsubstituted or substitutedcycloalkyl-Lx-amino, unsubstituted or substituted heteroaryl-Lx-amino,unsubstituted or substituted heterocycloalkyl-Lx-amino, unsubstituted orsubstituted alkylsulfonyl, unsubstituted or substituted alkenylsulfonyl, unsubstituted or substituted alkynylsulfonyl, unsubstituted orsubstituted aryl-Lx-sulfonyl, unsubstituted or substitutedcycloalkyl-Lx-sulfonyl, unsubstituted or substitutedheteroaryl-Lx-sulfonyl, unsubstituted or substitutedheterocycloalkyl-Lx-sulfonyl, unsubstituted or substituted alkylsulfonyl amino, unsubstituted or substituted alkenylsulfonylamino,unsubstituted or substituted alkynyl sulfonylamino, unsubstituted orsubstituted aryl-Lx-sulfonylamino, unsubstituted or substitutedcycloalkyl-Lx-sulfonylamino, unsubstituted or substitutedheteroaryl-Lx-sulfonylamino, unsubstituted or substitutedheterocycloalkyl-Lx-sulfonylamino, unsubstituted or substitutedalkylimino, unsubstituted or substituted alkenylimino, unsubstituted orsubstituted alkynylimino, unsubstituted or substituted aryl-Lx-imino,unsubstituted or substituted cycloalkyl-Lx-imino, unsubstituted orsubstituted heteroaryl-Lx-imino, unsubstituted or substitutedheterocycloalkyl-Lx-imino, unsubstituted or substituted alkyloxyimino,unsubstituted or substituted alkenyloxyimino, unsubstituted orsubstituted alkynyloxyimino, unsubstituted or substitutedaryl-Lx-oxyimino, unsubstituted or substituted cycloalkyl-Lx-oxyimino,unsubstituted or substituted heteroaryl-Lx-oxyimino, unsubstituted orsubstituted heterocycloalkyl-Lx-oxyimino, unsubstituted or substitutedalkyloxycarbonyl, unsubstituted or substituted alkenyloxycarbonyl,unsubstituted or substituted alkynyloxycarbonyl, unsubstituted orsubstituted aryl-Lx-oxycarbonyl, unsubstituted or substitutedcycloalkyl-Lx-oxycarbonyl, unsubstituted or substitutedheteroaryl-Lx-oxycarbonyl, unsubstituted or substitutedheterocycloalkyl-Lx-oxycarbonyl, unsubstituted or substitutedalkyloxycarbonylamino, unsubstituted or substitutedalkenyloxycarbonylamino, unsubstituted or substitutedalkynyloxycarbonylamino, unsubstituted or substitutedaryl-Lx-oxycarbonylamino, unsubstituted or substitutedcycloalkyl-Lx-oxycarbonylamino, unsubstituted or substitutedheteroaryl-Lx-oxycarbonylamino, unsubstituted or substitutedheterocycloalkyl-Lx-oxycarbonylamino, unsubstituted or substitutedalkylsulfanyl, unsubstituted or substituted alkenyl sulfanyl,unsubstituted or substituted alkynylsulfanyl, unsubstituted orsubstituted aryl-Lx-sulfanyl, unsubstituted or substitutedcycloalkyl-Lx-sulfanyl, unsubstituted or substitutedheteroaryl-Lx-sulfanyl, unsubstituted or substitutedheterocycloalkyl-Lx-sulfanyl, unsubstituted or substitutedalkylsulfinyl, unsubstituted or substituted alkenylsulfinyl,unsubstituted or substituted alkynylsulfinyl, unsubstituted orsubstituted aryl-Lx-sulfinyl, unsubstituted or substitutedcycloalkyl-Lx-sulfinyl, unsubstituted or substitutedheteroaryl-Lx-sulfinyl, unsubstituted or substitutedheterocycloalkyl-Lx-sulfinyl, unsubstituted or substitutedalkylcarbamoyl, unsubstituted or substituted alkenylcarbamoyl,unsubstituted or substituted alkynylcarbamoyl, unsubstituted orsubstituted aryl-Lx-carbamoyl, unsubstituted or substitutedcycloalkyl-Lx-carbamoyl, unsubstituted or substitutedheteroaryl-Lx-carbamoyl, unsubstituted or substitutedheterocycloalkyl-Lx-carbamoyl, unsubstituted or substituted alkylsulfamoyl, unsubstituted or substituted alkenylsulfamoyl, unsubstitutedor substituted alkynylsulfamoyl, unsubstituted or substitutedaryl-Lx-sulfamoyl, unsubstituted or substituted cycloalkyl-Lx-sulfamoyl,unsubstituted or substituted heteroaryl-Lx-sulfamoyl, and unsubstitutedor substituted heterocycloalkyl-Lx-sulfamoyl, wherein Lx is a singlebond or unsubstituted or substituted alkylene, wherein the substitutedalkyl, substituted alkenyl, substituted alkynyl, substituted aryl,substituted cycloalkyl, substituted heteroaryl, substitutedheterocycloalkyl, and substituted alkylene moieties (fully or partially)in the substituent group each independently have one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, hydroxy, oxo, carboxy, amino, imino,hydroxyamino, hydroxyimino, formyl, formyloxy, carbamoyl, sulfamoyl,sulfanyl, sulfino, sulfo, thioformyl, thiocarboxy, dithiocarboxy,thiocarbamoyl, cyano, nitro, nitroso, azide, hydrazino, ureide, amidino,amidinoamino, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl,heterocycloalkyl, alkyloxy, alkenyloxy, alkynyloxy, aryl-Lx-oxy,cycloalkyl-Lx-oxy, heteroaryl-Lx-oxy, heterocycloalkyl-Lx-oxy,alkyloxyalkyl, alkenyloxyalkyl, alkynyloxyalkyl, aryloxyalkyl,cycloalkyloxyalkyl, heteroaryloxyalkyl, heterocycloalkyloxyalkyl,alkyloxyalkyloxy, alkenyloxyalkyloxy, alkynyloxyalkyloxy,aryloxyalkyloxy, cycloalkyloxyalkyloxy, heteroaryloxyalkyloxy,heterocycloalkyloxyalkyloxy, alkylcarbonyl, alkenylcarbonyl,alkynylcarbonyl, aryl-Lx-carbonyl, cycloalkyl-Lx-carbonyl,heteroaryl-Lx-carbonyl, heterocycloalkyl-Lx-carbonyl, alkylcarbonyloxy,alkenylcarbonyloxy, alkynylcarbonyloxy, aryl-Lx-carbonyloxy,cycloalkyl-Lx-carbonyloxy, heteroaryl-Lx-carbonyloxy,heterocycloalkyl-Lx-carbonyloxy, alkylcarbonylamino,alkenylcarbonylamino, alkynylcarbonylamino, aryl-Lx-carbonylamino,cycloalkyl-Lx-carbonylamino, heteroaryl-Lx-carbonylamino,heterocycloalkyl-Lx-carbonylamino, alkylcarb onylthio,alkenylcarbonylthio, alkynylcarbonylthio, aryl-Lx-carbonylthio,cycloalkyl-Lx-carbonylthio, heteroaryl-Lx-carbonylthio,heterocycloalkyl-Lx-carbonylthio, alkylcarbonylimino,alkenylcarbonylimino, alkynylcarbonylimino, aryl-Lx-carbonylimino,cycloalkyl-Lx-carbonylimino, heteroaryl-Lx-carbonylimino,heterocycloalkyl-Lx-carbonylimino, alkylthio, alkenylthio, alkynylthio,aryl-Lx-thio, cycloalkyl-Lx-thio, heteroaryl-Lx-thio,heterocycloalkyl-Lx-thio, alkylamino, alkenylamino, alkynylamino,alkynylamino, aryl-Lx-amino, cycloalkyl-Lx-amino, heteroaryl-Lx-amino,heterocycloalkyl-Lx-amino, alkylsulfonyl, alkenyl sulfonyl,alkynylsulfonyl, aryl-Lx-sulfonyl, cycloalkyl-Lx-sulfonyl,heteroaryl-Lx-sulfonyl, heterocycloalkyl-Lx-sulfonyl, alkylsulfonylamino, alkenyl sulfonylamino, alkynylsulfonylamino,aryl-Lx-sulfonylamino, cycloalkyl-Lx-sulfonylamino,heteroaryl-Lx-sulfonylamino, heterocycloalkyl-Lx-sulfonylamino,alkylimino, alkenylimino, alkynylimino, aryl-Lx-imino,cycloalkyl-Lx-imino, heteroaryl-Lx-imino, heterocycloalkyl-Lx-imino,alkyloxyimino, alkenyloxyimino, alkynyloxyimino, aryl-Lx-oxyimino,cycloalkyl-Lx-oxyimino, heteroaryl-Lx-oxyimino,heterocycloalkyl-Lx-oxyimino, alkyloxycarbonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl-Lx-oxycarbonyl, cycloalkyl-Lx-oxycarbonyl,heteroaryl-Lx-oxycarbonyl, heterocycloalkyl-Lx-oxycarbonyl,alkyloxycarbonylamino, alkenyloxycarbonylamino, alkynyloxycarbonylamino,aryl-Lx-oxycarbonylamino, cycloalkyl-Lx-oxycarbonylamino,heteroaryl-Lx-oxycarbonylamino, heterocycloalkyl-Lx-oxycarbonylamino,alkylsulfanyl, alkenylsulfanyl, alkynylsulfanyl, aryl-Lx-sulfanyl,cycloalkyl-Lx-sulfanyl, heteroaryl-Lx-sulfanyl,heterocycloalkyl-Lx-sulfanyl, alkylsulfinyl, alkenylsulfinyl,alkynylsulfinyl, aryl-Lx-sulfinyl, cycloalkyl-Lx-sulfinyl,heteroaryl-Lx-sulfinyl, heterocycloalkyl-Lx-sulfinyl, alkylcarbamoyl,alkenylcarbamoyl, alkynylcarbamoyl, aryl-Lx-carbamoyl,cycloalkyl-Lx-carbamoyl, heteroaryl-Lx-carbamoyl,heterocycloalkyl-Lx-carbamoyl, alkylsulfamoyl, alkenylsulfamoyl,alkynylsulfamoyl, aryl-Lx-sulfamoyl, cycloalkyl-Lx-sulfamoyl,heteroaryl-Lx-sulfamoyl, and heterocycloalkyl-Lx-sulfamoyl.

Substituent group II consists of halogen, hydroxy, oxo, carboxy, amino,imino, hydroxyamino, hydroxyimino, formyl, formyloxy, carbamoyl,sulfamoyl, sulfanyl, sulfino, sulfo, thioformyl, thiocarboxy,dithiocarboxy, thiocarbamoyl, cyano, nitro, nitroso, azide, hydrazino,ureide, amidino, amidinoamino, unsubstituted or substituted C₁₋₁₂ alkyl,unsubstituted or substituted C₂₋₁₂ alkenyl, unsubstituted or substitutedC₂₋₁₂ alkynyl, unsubstituted or substituted C₆₋₁₀ aryl, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl, unsubstituted or substituted 5- to10-membered heteroaryl, unsubstituted or substituted 5- to 10-memberedheterocycloalkyl, unsubstituted or substituted C₁₋₁₂ alkyloxy,unsubstituted or substituted C₂₋₁₂ alkenyloxy, unsubstituted orsubstituted C₂₋₁₂ alkynyloxy, unsubstituted or substituted C₆₋₁₀aryl-Lx-oxy, unsubstituted or substituted C₃₋₁₀ cycloalkyl-Lx-oxy,unsubstituted or substituted 5- to 10-membered heteroaryl-Lx-oxy,unsubstituted or substituted 5- to 10-membered heterocycloalkyl-Lx-oxy,unsubstituted or substituted C₁₋₁₂ alkyloxy C₁₋₁₂ alkyl, unsubstitutedor substituted C₂₋₁₂ alkenyloxy C₁₋₁₂ alkyl, unsubstituted orsubstituted C₂₋₁₂ alkynyloxy C₁₋₁₂ alkyl, unsubstituted or substitutedC₆₋₁₀ aryloxy C₁₋₁₂ alkyl, unsubstituted or substituted C₃₋₁₀cycloalkyloxy C₁₋₁₂ alkyl, unsubstituted or substituted 5- to10-membered heteroaryloxy C₁₋₁₂ alkyl, unsubstituted or substituted 5-to 10-membered heterocycloalkyloxy C₁₋₁₂ alkyl, unsubstituted orsubstituted C₁₋₁₂ alkyloxy C₁₋₁₂ alkyloxy, unsubstituted or substitutedC₂₋₁₂ alkenyloxy C₁₋₁₂ alkyloxy, unsubstituted or substituted C₂₋₁₂alkynyloxy C₁₋₁₂ alkyloxy, unsubstituted or substituted C₆₋₁₀ aryloxyC₁₋₁₂ alkyloxy, unsubstituted or substituted C₃₋₁₀ cycloalkyloxy C₁₋₁₂alkyloxy, unsubstituted or substituted 5- to 10-membered heteroaryloxyC₁₋₁₂ alkyloxy, unsubstituted or substituted 5- to 10-memberedheterocycloalkyloxy C₁₋₁₂ alkyloxy, unsubstituted or substituted C₁₋₁₂alkylcarbonyl, unsubstituted or substituted C₂₋₁₂ alkenylcarbonyl,unsubstituted or substituted C₂₋₁₂ alkynylcarbonyl, unsubstituted orsubstituted C₆₋₁₀ aryl-Lx-carbonyl, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-carbonyl, unsubstituted or substituted 5- to 10-memberedheteroaryl-Lx-carbonyl, unsubstituted or substituted 5- to 10-memberedheterocycloalkyl-Lx-carbonyl, unsubstituted or substituted C₁₋₁₂alkylcarbonyloxy, unsubstituted or substituted C₂₋₁₂ alkenylcarbonyloxy,unsubstituted or substituted C₂₋₁₂ alkynylcarbonyloxy, unsubstituted orsubstituted C₆₋₁₀ aryl-Lx-carbonyloxy, unsubstituted or substitutedC₃₋₁₀ cy,cloalkyl-Lx-carbonyloxy, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-carbonyloxy, unsubstituted or substituted 5-to 10-membered heterocycloalkyl-Lx-carbonyloxy, unsubstituted orsubstituted C₁₋₁₂ alkylcarbonylamino, unsubstituted or substituted C₂₋₁₂alkenylcarbonylamino, unsubstituted or substituted C₂₋₁₂alkynylcarbonylamino, unsubstituted or substituted C₆₋₁₀aryl-Lx-carbonylamino, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-carbonylamino, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-carbonylamino, unsubstituted or substituted 5-to 10-membered heterocycloalkyl-Lx-carbonylamino, unsubstituted orsubstituted C₁₋₁₂ alkylcarbonylthio, unsubstituted or substituted C₂₋₁₂alkenylcarbonylthio, unsubstituted or substituted C₂₋₁₂alkynylcarbonylthio, unsubstituted or substituted C₆₋₁₀aryl-Lx-carbonylthio, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-carbonylthio, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-carbonylthio, unsubstituted or substituted 5-to 10-membered heterocycloalkyl-Lx-carbonylthio, unsubstituted orsubstituted C₁₋₁₂ alkylcarbonylimino, unsubstituted or substituted C₂₋₁₂alkenylcarbonylimino, unsubstituted or substituted C₂₋₁₂alkynylcarbonylimino, unsubstituted or substituted C₆₋₁₀aryl-Lx-carbonylimino, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-carbonylimino, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-carbonylimino, unsubstituted or substituted 5-to 10-membered heterocycloalkyl-Lx-carbonylimino, unsubstituted orsubstituted C₁₋₁₂ alkylthio, unsubstituted or substituted C₂₋₁₂alkenylthio, unsubstituted or substituted C₂₋₁₂ alkynylthio,unsubstituted or substituted C₆₋₁₀ aryl-Lx-thio, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl-Lx-thio, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-thio, unsubstituted or substituted 5- to10-membered heterocycloalkyl-Lx-thio, unsubstituted or substituted C₁₋₁₂alkylamino, unsubstituted or substituted C₂₋₁₂ alkenylamino,unsubstituted or substituted C₂₋₁₂ alkynylamino, unsubstituted orsubstituted C₂₋₁₂ alkynylamino, unsubstituted or substituted C₆₋₁₀aryl-Lx-amino, unsubstituted or substituted C₃₋₁₀ cycloalkyl-Lx-amino,unsubstituted or substituted 5- to 10-membered heteroaryl-Lx-amino,unsubstituted or substituted 5- to 10-memberedheterocycloalkyl-Lx-amino, unsubstituted or substituted C₁₋₁₂alkylsulfonyl, unsubstituted or substituted C₂₋₁₂ alkenylsulfonyl,unsubstituted or substituted C₂₋₁₂ alkynylsulfonyl, unsubstituted orsubstituted C₆₋₁₀ aryl-Lx-sulfonyl, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-sulfonyl, unsubstituted or substituted 5- to 10-memberedheteroaryl-Lx-sulfonyl, unsubstituted or substituted 5- to 10-memberedheterocycloalkyl-Lx-sulfonyl, unsubstituted or substituted C₁₋₁₂alkylsulfonylamino, unsubstituted or substituted C₂₋₁₂ alkenylsulfonylamino, unsubstituted or substituted C₂₋₁₂ alkynyl sulfonylamino,unsubstituted or substituted C₆₋₁₀ aryl-Lx-sulfonylamino, unsubstitutedor substituted C₃₋₁₀ cycloalkyl-Lx-sulfonylamino, unsubstituted orsubstituted 5- to 10-membered heteroaryl-Lx-sulfonylamino, unsubstitutedor substituted 5- to 10-membered heterocycloalkyl-Lx-sulfonylamino,unsubstituted or substituted C₁₋₁₂ alkylimino, unsubstituted orsubstituted C₂₋₁₂ alkenylimino, unsubstituted or substituted C₂₋₁₂alkynylimino, unsubstituted or substituted C₆₋₁₀ aryl-Lx-imino,unsubstituted or substituted C₃₋₁₀ cycloalkyl-Lx-imino, unsubstituted orsubstituted 5- to 10-membered heteroaryl-Lx-imino, unsubstituted orsubstituted 5- to 10-membered heterocycloalkyl-Lx-imino, unsubstitutedor substituted C₁₋₁₂ alkyloxyimino, unsubstituted or substituted C₂₋₁₂alkenyloxyimino, unsubstituted or substituted C₂₋₁₂ alkynyloxyimino,unsubstituted or substituted C₆₋₁₀ aryl-Lx-oxyimino, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl-Lx-oxyimino, unsubstituted or substituted5- to 10-membered heteroaryl-Lx-oxyimino, unsubstituted or substituted5- to 10-membered heterocycloalkyl-Lx-oxyimino, unsubstituted orsubstituted C₁₋₁₂ alkyloxycarbonyl, unsubstituted or substituted C₂₋₁₂alkenyloxycarbonyl, unsubstituted or substituted C₂₋₁₂alkynyloxycarbonyl, unsubstituted or substituted C₆₋₁₀aryl-Lx-oxycarbonyl, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-oxycarbonyl, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-oxycarbonyl, unsubstituted or substituted 5-to 10-membered heterocycloalkyl-Lx-oxycarbonyl, unsubstituted orsubstituted C₁₋₁₂ alkyloxycarbonylamino, unsubstituted or substitutedC₂₋₁₂ alkenyloxycarbonylamino, unsubstituted or substituted C₂₋₁₂alkynyloxycarbonylamino, unsubstituted or substituted C₆₋₁₀aryl-Lx-oxycarbonylamino, unsubstituted or substituted C₃₋₁₀cycloalkyl-Lx-oxycarbonylamino, unsubstituted or substituted 5- to10-membered heteroaryl-Lx-oxycarbonylamino, unsubstituted or substituted5- to 10-membered heterocycloalkyl-Lx-oxycarbonylamino, unsubstituted orsubstituted C₁₋₁₂ alkylsulfanyl, unsubstituted or substituted C₂₋₁₂alkenylsulfanyl, unsubstituted or substituted C₂₋₁₂ alkynylsulfanyl,unsubstituted or substituted C₆₋₁₀ aryl-Lx-sulfanyl, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl-Lx-sulfanyl, unsubstituted or substituted5- to 10-membered heteroaryl-Lx-sulfanyl, unsubstituted or substituted5- to 10-membered heterocycloalkyl-Lx-sulfanyl, unsubstituted orsubstituted C₁₋₁₂ alkylsulfinyl, unsubstituted or substituted C₂₋₁₂alkenylsulfinyl, unsubstituted or substituted C₂₋₁₂ alkynylsulfinyl,unsubstituted or substituted C₆₋₁₀ aryl-Lx-sulfinyl, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl-Lx-sulfinyl, unsubstituted or substituted5- to 10-membered heteroaryl-Lx-sulfinyl, unsubstituted or substituted5- to 10-membered heterocycloalkyl-Lx-sulfinyl, unsubstituted orsubstituted C₁₋₁₂ alkylcarbamoyl, unsubstituted or substituted C₂₋₁₂alkenylcarbamoyl, unsubstituted or substituted C₂₋₁₂ alkynylcarbamoyl,unsubstituted or substituted C₆₋₁₀ aryl-Lx-carbamoyl, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl-Lx-carbamoyl, unsubstituted or substituted5- to 10-membered heteroaryl-Lx-carbamoyl, unsubstituted or substituted5- to 10-membered heterocycloalkyl-Lx-carbamoyl, unsubstituted orsubstituted C₁₋₁₂ alkyl sulfamoyl, unsubstituted or substituted C₂₋₁₂alkenylsulfamoyl, unsubstituted or substituted C₂₋₁₂ alkynylsulfamoyl,unsubstituted or substituted C₆₋₁₀ aryl-Lx-sulfamoyl, unsubstituted orsubstituted C₃₋₁₀ cycloalkyl-Lx-sulfamoyl, unsubstituted or substituted5- to 10-membered heteroaryl-Lx-sulfamoyl, and unsubstituted orsubstituted 5- to 10-membered heterocycloalkyl-Lx-sulfamoyl, wherein Lxis a single bond or unsubstituted or substituted C₁₋₁₂ alkylene,

wherein the substituted C₁₋₁₂ alkyl, substituted C₂₋₁₂ alkenyl,substituted C₂₋₁₂ alkynyl, substituted C₆₋₁₀ aryl, substituted C₃₋₁₀cycloalkyl, substituted 5- to 10-membered heteroaryl, substituted 5- to10-membered heterocycloalkyl, and substituted alkylene moieties (fullyor partially) in the substituent group each independently have one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of halogen, hydroxy, oxo, carboxy,amino, imino, hydroxyamino, hydroxyimino, formyl, formyloxy, carbamoyl,sulfamoyl, sulfanyl, sulfino, sulfo, thioformyl, thiocarboxy,dithiocarboxy, thiocarbamoyl, cyano, nitro, nitroso, azide, hydrazino,ureide, amidino, amidinoamino, C₁₋₁₂ alkyl, C₁₋₁₂ haloalkyl, C₂₋₁₂alkenyl, C₂₋₁₂ alkynyl, C₆₋₁₀ aryl, C₃₋₁₀ cycloalkyl, 5- to 10-memberedheteroaryl, 5- to 10-membered heterocycloalkyl, C₁₋₁₂ alkyloxy, C₁₋₁₂haloalkyloxy, C₂₋₁₂ alkenyloxy, C₂₋₁₂ alkynyloxy, C₆₋₁₀ aryl-Lx-oxy,C₃₋₁₀ cycloalkyl-Lx-oxy, 5- to 10-membered heteroaryl-Lx-oxy, 5- to10-membered heterocycloalkyl-Lx-oxy, C₁₋₁₂ alkyloxyalkyl, C₂₋₁₂alkenyloxyalkyl, C₂₋₁₂ alkynyloxyalkyl, C₆₋₁₀ aryloxyalkyl, C₃₋₁₀cycloalkyloxyalkyl, 5- to 10-membered heteroaryloxyalkyl, 5- to10-membered heterocycloalkyloxyalkyl, C₁₋₁₂ alkyloxyalkyloxy, C₂₋₁₂alkenyloxyalkyloxy, C₂₋₁₂ alkynyloxyalkyloxy, C₆₋₁₀ aryloxyalkyloxy,C₃₋₁₀ cycloalkyloxyalkyloxy, 5- to 10-membered heteroaryloxyalkyloxy, 5-to 10-membered heterocycloalkyloxyalkyloxy, C₁₋₁₂ alkylcarbonyl, C₂₋₁₂alkenylcarbonyl, C₂₋₁₂ alkynylcarbonyl, C₆₋₁₀ aryl-Lx-carbonyl, C₃₋₁₀cycloalkyl-Lx-carbonyl, 5- to 10-membered heteroaryl-Lx-carbonyl, 5- to10-membered heterocycloalkyl-Lx-carbonyl, C₁₋₁₂ alkylcarbonyloxy, C₂₋₁₂alkenylcarbonyloxy, C₂₋₁₂ alkynylcarbonyloxy, C₆₋₁₀ aryl-Lx-carbonyloxy,C₃₋₁₀ cycloalkyl-Lx-carbonyloxy, 5- to 10-memberedheteroaryl-Lx-carbonyloxy, 5- to 10-memberedheterocycloalkyl-Lx-carbonyloxy, C₁₋₁₂ alkylcarbonylamino, C₂₋₁₂alkenylcarbonylamino, C₂₋₁₂ alkynylcarbonylamino, C₆₋₁₀aryl-Lx-carbonylamino, C₃₋₁₀ cycloalkyl-Lx-carbonylamino, 5- to10-membered heteroaryl-Lx-carbonylamino, 5- to 10-memberedheterocycloalkyl-Lx-carbonylamino, C₁₋₁₂ alkylcarbonylthio, C₂₋₁₂alkenylcarbonylthio, C₂₋₁₂ alkynylcarbonylthio, C₆₋₁₀aryl-Lx-carbonylthio, C₃₋₁₀ cycloalkyl-Lx-carbonylthio, 5- to10-membered heteroaryl-Lx-carbonylthio, 5- to 10-memberedheterocycloalkyl-Lx-carbonylthio, C₁₋₁₂ alkylcarbonylimino, C₂₋₁₂alkenylcarbonylimino, C₂₋₁₂ alkynylcarbonylimino, C₆₋₁₀aryl-Lx-carbonylimino, C₃₋₁₀ cycloalkyl-Lx-carbonylimino, 5- to10-membered heteroaryl-Lx-carbonylimino, 5- to 10-memberedheterocycloalkyl-Lx-carbonylimino, C₁₋₁₂ alkylthio, C₂₋₁₂ alkenylthio,C₂₋₁₂ alkynylthio, C₆₋₁₀ aryl-Lx-thio, C₃₋₁₀ cycloalkyl-Lx-thio, 5- to10-membered heteroaryl-Lx-thio, 5- to 10-memberedheterocycloalkyl-Lx-thio, C₁₋₁₂ alkylamino, C₂₋₁₂ alkenylamino, C₂₋₁₂alkynylamino, C₂₋₁₂ alkynylamino, C₆₋₁₀ aryl-Lx-amino, C₃₋₁₀cycloalkyl-Lx-amino, 5- to 10-membered heteroaryl-Lx-amino, 5- to10-membered heterocycloalkyl-Lx-amino, C₁₋₁₂ alkylsulfonyl, C₂₋₁₂alkenylsulfonyl, C₂₋₁₂ alkynylsulfonyl, C₆₋₁₀ aryl-Lx-sulfonyl, C₃₋₁₀cycloalkyl-Lx-sulfonyl, 5- to 10-membered heteroaryl-Lx-sulfonyl, 5- to10-membered heterocycloalkyl-Lx-sulfonyl, C₁₋₁₂ alkyl sulfonyl amino,C₂₋₁₂ alkenyl sulfonyl amino, C₂₋₁₂ alkynylsulfonylamino, C₆₋₁₀aryl-Lx-sulfonylamino, C₃₋₁₀ cycloalkyl-Lx-sulfonylamino, 5- to10-membered heteroaryl-Lx-sulfonylamino, 5- to 10-memberedheterocycloalkyl-Lx-sulfonylamino, C₁₋₁₂ alkylimino, C₂₋₁₂ alkenylimino,C₂₋₁₂ alkynylimino, C₆₋₁₀ aryl-Lx-imino, C₃₋₁₀ cycloalkyl-Lx-imino, 5-to 10-membered heteroaryl-Lx-imino, 5- to 10-memberedheterocycloalkyl-Lx-imino, C₁₋₁₂ alkyloxyimino, C₂₋₁₂ alkenyloxyimino,C₂₋₁₂ alkynyloxyimino, C₆₋₁₀ aryl-Lx-oxyimino, C₃₋₁₀cycloalkyl-Lx-oxyimino, 5- to 10-membered heteroaryl-Lx-oxyimino, 5- to10-membered heterocycloalkyl-Lx-oxyimino, C₁₋₁₂ alkyloxycarbonyl, C₂₋₁₂alkenyloxycarbonyl, C₂₋₁₂ alkynyloxycarbonyl, C₆₋₁₀ aryl-Lx-oxycarbonyl,C₃₋₁₀ cycloalkyl-Lx-oxycarbonyl, 5- to 10-memberedheteroaryl-Lx-oxycarbonyl, 5- to 10-memberedheterocycloalkyl-Lx-oxycarbonyl, C₁₋₁₂ alkyloxycarbonylamino, C₂₋₁₂alkenyloxycarbonylamino, C₂₋₁₂ alkynyloxycarbonylamino, C₆₋₁₀aryl-Lx-oxycarbonylamino, C₃₋₁₀ cycloalkyl-Lx-oxycarbonylamino, 5- to10-membered heteroaryl-Lx-oxycarbonylamino, 5- to 10-memberedheterocycloalkyl-Lx-oxycarbonylamino, C₁₋₁₂ alkyl sulfanyl, C₂₋₁₂alkenyl sulfanyl, C₂₋₁₂ alkynyl sulfanyl, C₆₋₁₀ aryl-Lx-sulfanyl, C₃₋₁₀cycloalkyl-Lx-sulfanyl, 5- to 10-membered heteroaryl-Lx-sulfanyl, 5- to10-membered heterocycloalkyl-Lx-sulfanyl, C₁₋₁₂ alkylsulfinyl, C₂₋₁₂alkenylsulfinyl, C₂₋₁₂ alkynylsulfinyl, C₆₋₁₀ aryl-Lx-sulfinyl, C₃₋₁₀cycloalkyl-Lx-sulfinyl, 5- to 10-membered heteroaryl-Lx-sulfinyl, 5- to10-membered heterocycloalkyl-Lx-sulfinyl, C₁₋₁₂ alkylcarbamoyl, C₂₋₁₂alkenylcarbamoyl, C₂₋₁₂ alkynylcarbamoyl, C₆₋₁₀ aryl-Lx-carbamoyl, C₃₋₁₀cycloalkyl-Lx-carbamoyl, 5- to 10-membered heteroaryl-Lx-carbamoyl, 5-to 10-membered heterocycloalkyl-Lx-carbamoyl, C₁₋₁₂ alkylsulfamoyl,C₂₋₁₂ alkenylsulfamoyl, C₂₋₁₂ alkynylsulfamoyl, C₆₋₁₀ aryl-Lx-sulfamoyl,C₃₋₁₀ cycloalkyl-Lx-sulfamoyl, 5- to 10-memberedheteroaryl-Lx-sulfamoyl, and 5- to 10-memberedheterocycloalkyl-Lx-sulfamoyl. [0021]

Substituent group III consists of halogen, hydroxy, carboxy, amino,carbamoyl, nitro, amidinoamino, alkyl, aryl, cycloalkyl, heteroaryl,alkyloxy, alkylcarbonyl, cycloalkylcarbonyl, alkylcarbonylamino,cycloalkylcarbonylamino, alkylamino, cycloalkylalkylamino,alkyloxycarbonyl, and trialkylsilyloxy, and these groups of thesubstituent group are optionally substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, hydroxy, carboxy, amino, carbamoyl,nitro, alkyl, haloalkyl, alkyloxy, haloalkyloxy, and alkyloxycarbonyl.

Substituent group III is preferably substituent group III', whichconsists of halogen, hydroxy, carboxy, amino, carbamoyl, nitro,amidinoamino, C₁₋₁₂ alkyl, C₆₋₁₀ aryl, C₃₋₁₀ cycloalkyl, 5- to10-membered heteroaryl, C₁₋₁₂ alkyloxy, C₁₋₁₂ alkylcarbonyl, C₃₋₁₀cycloalkylcarbonyl, C₁₋₁₂ alkylcarbonylamino, C₃₋₁₀cycloalkylcarbonylamino, C₁₋₁₂ alkylamino, C₃₋₁₀ cycloalkyl C₁₋₆alkylamino, C₁₋₁₂ alkyloxycarbonyl, and tri-C₁₋₆ alkylsilyloxy, whereinthese groups of the substituent group are optionally substituted withone to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, hydroxy,carboxy, amino, carbamoyl, nitro, C₁₋₁₂ alkyl, C₁₋₁₂ haloalkyl, C₁₋₁₂alkyloxy, C₁₋₁₂ haloalkyloxy, and C₁₋₁₂ alkyloxycarbonyl.

Substituent group IV consists of halogen, hydroxy, carboxy, amino,carbamoyl, nitro, amidino, alkyl, aryl, cycloalkyl,heteroarylheterocycloalkyl, arylalkyl, cycloalkylalkyl, alkyloxy,aryloxy, alkylcarbonyl, cycloalkylcarbonyl, alkyloxycarbonyl, andtrialkylsilyloxy, and these groups of the substituent group areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, hydroxy, carboxy, amino, carbamoyl, nitro, alkyl, haloalkyl,alkyloxy, haloalkyloxy, and alkyloxycarbonyl.

Substituent group IV is preferably substituent group IV', which consistsof halogen, hydroxy, carboxy, amino, carbamoyl, nitro, amidino, C₁₋₆alkyl, C₆₋₁₀ aryl, C₃₋₁₀ cycloalkyl, 5- to 10-membered heteroaryl, 5- to10-membered heterocycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₃₋₁₀ cycloalkylC₁₋₆ alkyl, C₁₋₆ alkyloxy, C₆₋₁₀ aryloxy, C₁₋₆ alkylcarbonyl, C₃₋₁₀cycloalkylcarbonyl, C₁₋₆ alkyloxycarbonyl, and tri-C₁₋₆ alkylsilyloxy,and these groups of the substituent group are each independently andoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, hydroxy, carboxy, amino, carbamoyl, nitro, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkyloxy, C₁₋₆ haloalkyloxy, and C₁₋₆ alkyloxycarbonyl.

Substituent group V consists of halogen, hydroxy, carboxy, amino,formyl, carbamoyl, cyano, nitro, amidino, amidinoamino, alkyl, aryl,cycloalkyl, heteroaryl, heterocycloalkyl, alkyloxy, aryloxy,cycloalkyloxy, heteroaryloxy, heterocycloalkyloxy, alkyloxyoxy,alkylamino, arylamino, cycloalkylamino, heteroarylamino,heterocycloalkylamino, formyl, alkylcarbonyl, arylcarbonyl,cycloalkylcarbonyl, heteroarylcarbonyl, heterocycloalkylcarbonyl,alkyloxycarbonyl, aryloxycarbonyl, cycloalkyloxycarbonyl,heteroaryloxycarbonyl, heterocycloalkyloxycarbonyl, alkylcarbamoyl,arylcarbamoyl, cycloalkylcarbamoyl, heteroarylcarbamoyl, andheterocycloalkylcarbamoyl, wherein these groups of the substituent groupare each independently and optionally substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, hydroxy, carboxy, amino,formyl, carbamoyl, cyano, nitro, amidino, amidinoamino, alkyl, alkyloxy,haloalkyl, haloalkyloxy, alkylamino, formyl, alkylcarbonyl,alkyloxycarbonyl, and alkylcarbamoyl.

Substituent group V is preferably substituent group V′, which consistsof halogen, hydroxy, carboxy, amino, formyl, carbamoyl, cyano, nitro,amidino, amidinoamino, C₁₋₁₂ alkyl, C₆₋₁₀ aryl, C₃₋₁₀ cycloalkyl, 5- to10-membered heteroaryl, 5- to 10-membered heterocycloalkyl, C₁₋₁₂alkyloxy, C₆₋₁₀ aryloxy, C₃₋₁₀ cycloalkyloxy, 5- to 10-memberedheteroaryloxy, 5- to 10-membered heterocycloalkyloxy, C₁₋₁₂ alkylamino,C₆₋₁₀ arylamino, C₃₋₁₀ cycloalkylamino, 5- to 10-memberedheteroarylamino, 5- to 10-membered heterocycloalkylamino, formyl, C₁₋₁₂alkylcarbonyl, C₆₋₁₀ arylcarbonyl, C₃₋₁₀ cycloalkylcarbonyl, 5- to10-membered heteroarylcarbonyl, 5- to 10-memberedheterocycloalkylcarbonyl, C₁₋₁₂ alkyloxycarbonyl, C₆₋₁₀ aryloxycarbonyl,C₃₋₁₀ cycloalkyloxycarbonyl, 5- to 10-membered heteroaryloxycarbonyl, 5-to 10-membered heterocycloalkyloxycarbonyl, C₁₋₁₂ alkylcarbamoyl, C₆₋₁₀arylcarbamoyl, C₃₋₁₀ cycloalkylcarbamoyl, 5- to 10-memberedheteroarylcarbamoyl, and 5- to 10-membered heterocycloalkylcarbamoyl,wherein these groups of the substituent group are each independently andoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, hydroxy, carboxy, amino, formyl, carbamoyl, cyano, nitro,amidino, amidinoamino, C₁₋₆ alkyl, C₁₋₆ alkyloxy, C₁₋₆ haloalkyl, C₁₋₆haloalkyloxy, C₁₋₆ alkylamino, formyl, C₁₋₆ alkylcarbonyl, C₁₋₆alkyloxycarbonyl, and C₁₋₆ alkylcarbamoyl.

Substituent group VI consists of halogen, hydroxy, carboxy, amino,formyl, carbamoyl, cyano, nitro, amidino, amidinoamino, alkyl, alkyloxy,haloalkyl, haloalkyloxy, alkylamino, formyl, alkylcarbonyl,alkyloxycarbonyl, and alkylcarbamoyl.

Substituent group VI is preferably substituent group VI', which consistsof halogen, hydroxy, carboxy, amino, formyl, carbamoyl, cyano, nitro,amidino, amidinoamino, C₁₋₆ alkyl, C₁₋₆ alkyloxy, C₁₋₆ haloalkyl, C₁₋₆haloalkyloxy, C₁₋₆ alkylamino, formyl, C₁₋₆ alkylcarbonyl, C₁₋₆alkyloxycarbonyl, and C₁₋₆ alkylcarbamoyl.

As used herein, examples of substituents used when “optionallysubstituted” include substituent group a and substituent group β.Substituent group α can be substituent group α1, substituent group α2,or substituent group α3. Substituent group β can be substituent groupβ1, substituent group β2, or substituent group β3. Substituents usedwhen “optionally substituted” can be selected from substituent group α1,and substitution can be performed with 1 to 5 of the same or differentsubstituents. While the types of atoms within a substituent associatedwith attachment are not particularly limited by the type of substituent,if the atom to which a substituent attaches is an oxygen atom, anitrogen atom, or a sulfur atom, the sub stituent is limited to thosewith an attaching atom that is a carbon atom from the followingsubstituents.

Substituent group α1 includes

-   1) halogen atom-   2) hydroxyl group-   3) carboxyl group-   4) cyano group-   5) C₁₋₆ alkyl-   6) C₂₋₆ alkenyl-   7) C₂₋₆ alkynyl-   8) C₁₋₆ alkoxy-   9) C₁₋₆ alkylthio-   10) C₁₋₆ alkylcarbonyl-   11) C₁₋₆ alkylsulfonyl    (however, each substituent from 5) to 11) is optionally substituted    with 1 to 5 of the same or different substituents selected from    substituent group β1)-   12) C₃₋₁₀ alicyclic group-   13) C₃₋₁₀ alicyclic oxy-   14) C₆₋₁₀ aryloxy-   15) 5- to 6-membered heteroaryloxy-   16) 4- to 10-membered non-aryl heterocyclyloxy-   17) C₃₋₁₀ alicyclic thio-   18) C₆₋₁₀ arylthio-   19) 5- to 6-membered heteroarylthio-   20) 4- to 10-membered non-aryl heterocyclylthio-   21) C₆₋₁₀ aryl-   22) 5- to 6-membered heteroaryl-   23) 4- to 10-membered non-aryl heterocycle-   24) C₃₋₁₀ alicyclic carbonyl-   25) C₆₋₁₀ arylcarbonyl-   26) 5- to 6-membered heteroarylcarbonyl-   27) 4- to 10-membered non-aryl heterocyclylcarbonyl-   28) C₃₋₁₀ alicyclic sulfonyl-   29) C₆₋₁₀ aryl sulfonyl-   30) 5- to 6-membered heteroarylsulfonyl-   31) 4- to 10-membered non-aryl heterocyclylsulfonyl    (however, each substituent from 12) to 31) is optionally substituted    with 1 to 5 substituents in substituent group (31 or 5) C₁₋₆ alkyl)-   32) —NR^(10a)R^(11a)-   33) —SO₂—NR^(10b)R^(11b)-   34) —NR^(10c)—C(═O)R^(11c)-   35) —NR^(10d)—C(═O)OR^(11d)-   36) —NR^(12a)—C(═O)NR^(10e)R^(11e)-   37) —NR^(10i)—SO₂ 13 R^(11i)-   38) —NR^(12c)—SO₂—NR^(10j)R^(11j)-   39) —C(═O)OR^(10k)-   40) —C(═O)NR^(10l)R^(11k)-   41) —C(═O)NR^(10m)OR^(11l)-   42) —C(═O)NR^(12d)—NR^(10n)R^(11m)-   43) —C(═NR^(13a))R^(10s)-   44) —C(═NR^(13c))NR^(10t)R^(11q)-   45) —C(═NR^(13d))NR^(12f)—NR^(10u)R^(11r)-   46) —NR^(17c)—C(═NR^(13k))R^(17d)-   47) —NR^(12g)—C(═NR^(13e))—NR^(10v)R^(11s)-   48) —NR¹⁴—C(═NR^(13f))—NR^(12h)—NR^(10w)R^(11t)-   49) —OC(═O)R^(10x)-   50) —OC(═O)OR^(10y)-   51) —OC(═O)NR^(10z1)R^(11a)-   52) —NR^(12i)—NR^(10z2)R^(11v)-   53) —NR^(10z3)OR^(11w), and-   54) protecting group, and

substituent group β1 is a group consisting of

-   1) halogen atom,-   2) hydroxyl group,-   3) carboxyl group,-   4) cyano group,-   5) C₃₋₁₀ alicyclic group,-   6) C₁₋₆ alkoxy,-   7) C₃₋₁₀ alicyclic oxy,-   8) C₁₋₆ alkylthio,-   9) 5- to 6-membered heteroarylthio,-   10) C₆₋₁₀ aryl,-   11) 5- to 6-membered heteroaryl,-   12) 4- to 10-membered non-aryl heterocycle,-   13) C₁₋₆ alkylcarbonyl,-   14) C₃₋₁₀ alicyclic carbonyl,-   15) C₆₋₁₀ arylcarbonyl,-   16) 5- to 6-membered heteroarylcarbonyl,-   17) 4- to 10-membered non-aryl heterocyclylcarbonyl,-   18) —NR^(15a)R^(16a),-   19) —SO₂—NR^(15b)R^(16b),-   20) —NR^(15c)—C(═O)R^(16c)-   21) —NR^(17a)—C(═O)NR^(15d)R^(16d),-   22) —C(═O)NR^(15e)R^(16e),-   23) —C(═NR^(13g))R^(15f),-   24) —C(═NR^(13h))NR^(15g)R^(16f)-   25) —NR^(16g)—C(═NR^(13i))R^(15h)-   26) —NR^(17h)—C(═NR^(13j))—NR^(15i)R^(16h), and-   27) protecting group    (however, each substituent from 5) to 17) in substituent group β1 is    optionally substituted with 1 to 5 substituents selected from the    group consisting of a halogen atom, hydroxyl group, cyano group,    carboxyl group, and —NR^(18a)R^(18b)), wherein

R^(13a), R^(13a2), R^(13c), R^(13c2), R^(13d), R^(13d2), R^(13e),R^(13f), R^(13g), R^(13g2), R^(13h), R^(13h2), R^(13i), R^(13j), andR^(13k) are each independently the same or different hydrogen atom,hydroxyl group, C₁₋₆ alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkoxycarbonyl,

R^(10a), R^(10b), R^(10c), R^(10d), R^(10e), R^(10i), R^(10j), R^(10k),R^(10l), R^(10m), R^(10n), R^(10s), R^(10s2), R^(10t), R^(10t2),R^(10u), R^(10u2), R^(10v), R^(10w), R^(10x), R^(10y), R^(10z1),R^(10z2), R^(10z3), R^(11a), R^(11b), R^(11c), R^(11d), R^(11e),R^(11i), R^(11j), R^(11k), R^(11l), R^(11m), R^(11q), R^(11q2), R^(11r),R^(11r2), R^(11s), R^(11t), R^(11u), R^(11v), R^(11w), R^(12a), R^(12c),R^(12d), R^(12f), R^(12f2), R^(12g), R^(12h), R^(12i), R¹⁴, R^(15a),R^(15b), R^(15c), R^(15d), R^(15e), R^(15f), R^(15f2), R^(15g),R^(15g2), R^(15h), R^(15i), R^(16a), R^(16b), R^(16c), R^(16d), R^(16e),R^(16f), R^(16f2), R^(16g), R^(16h), R^(17a), R^(17b), R^(17c), andR^(17d) are each independently the same or different hydrogen atom, C₁₋₆alkyl (the C₁₋₆ alkyl is optionally substituted with 1 to 3 of the sameor different substituents selected from a hydroxyl group, cyano group,C₁₋₆ alkoxy, and —NR^(18a)R^(18b)), or C₁₋₆ alkoxycarbonyl, and

R^(18a) and R^(18b) are each independently the same or differenthydrogen atom or C₁₋₆ alkyl.

In an exemplary embodiment, hydrogen of any hydroxyl group insubstituent groups α1 and β1 is optionally substituted with a protectinggroup.

Examples of preferred substituents as the substituent used when“optionally substituted” herein include the following.

Substituent group a2 preferably includes

-   1) halogen atom-   2) hydroxyl group-   3) carboxyl group-   4) cyano group-   5) C₁₋₆ alkyl-   6) C₁₋₆ alkoxy-   7) C₁₋₆ alkylthio-   8) C₁₋₆ alkylcarbonyl    (however, each substituent from 5) to 8) is optionally substituted    with 1 to 5 same or different substituents selected from substituent    group β2)-   9) C₃₋₁₀ alicyclic group-   10) C₃₋₁₀ alicyclic oxy-   11) C₆₋₁₀ aryloxy-   12) 5- to 6-membered heteroaryloxy-   13) 4- to 10-membered non-aryl heterocyclyloxy-   14) C₃₋₁₀ alicyclic thio-   15) C₆₋₁₀ arylthio-   16) 5- to 6-membered heteroarylthio-   17) 4- to 10-membered non-aryl heterocyclylthio-   18) C₆₋₁₀ aryl-   19) 5- to 6-membered heteroaryl-   20) 4- to 10-membered non-aryl heterocycle-   21) C₃₋₁₀ alicyclic carbonyl-   22) C₆₋₁₀ arylcarbonyl-   23) 5- to 6-membered heteroarylcarbonyl-   24) 4- to 10-membered non-aryl heterocyclylcarbonyl    (however, each substituent from 9) to 24) is optionally substituted    with 1 to 5 substituents in substituent group β2 or 1) C₁₋₆ alkyl)-   25) —NR^(10a)R^(11a)-   26) —SO₂—NR^(10b)R^(11b)-   27) —NR^(10c)—C(═O)R^(11c)-   28) —NR^(12a)—C(═O)NR^(10d)R^(11d)-   29) —NR^(10e)—SO₂—R^(11e)-   30) —NR^(12b)—SO₂—NR^(10f)R^(11f)-   31) —C(═O)NR^(10g)R^(11g)-   32) —C(═NR^(13a))R^(10h)-   33) —C(═NR^(13b))NR^(10i)R^(11h)-   34) —NR^(11f2)—C(═NR^(13c))R^(10g2), and-   35) —NR^(12c)—C(═NR^(13d))—NR^(10j)R^(11i), and

substituent group β2 is preferably a group consisting of

-   1) halogen atom-   2) hydroxyl group-   3) cyano group-   4) C₃₋₁₀ alicyclic group-   5) C₁₋₆ alkoxy-   6) C₁₋₆ alkylthio-   7) 5- to 6-membered heteroarylthio-   8) 5- to 6-membered heteroaryl-   9) 4- to 10-membered non-aryl heterocycle-   10) C₁₋₆ alkylcarbonyl-   11) C₃₋₁₀ alicyclic carbonyl-   12) C₆₋₁₀ arylcarbonyl-   13) 5- to 6-membered heteroarylcarbonyl-   14) 4- to 10-membered non-aryl heterocyclylcarbonyl-   15) —NR^(15a)R^(16a)-   16) —NR^(15b)—C(═O)R^(16b)-   17) —NR^(17a)—C(═O)NR^(15c)R^(16c)-   18) —C(═O)NR^(15d)R^(16d)-   19) —C(═NR^(13e))R^(15e)-   20) —C(═NR^(13f))NR^(15f)R^(16e)-   21) —NR^(16f)—C(═NR^(13g))R^(15g)-   22) —NR^(17b)—C(═NR^(13h))—NR^(15h)R^(16g)-   23) —C(═N—OR^(13e2))R^(15e2), and-   24) —C(═N—OR^(13f2))NR^(15f2)R^(16e2)    (however, each substituent from 4) to 14) in substituent group β2 is    optionally substituted with 1 to 5 substituents selected from the    group consisting of a halogen atom, hydroxyl group, cyano group,    carboxyl group, and —NR^(18a)R^(18b),

R^(13a), R^(13a2), R^(13b), R^(13b2), R^(13c), R^(13d), R^(13e),R^(13e2), R^(13f), R^(13f2), R^(13g), and R^(13h) are each independentlythe same or different hydrogen atom, hydroxyl group, C₁₋₆ alkyl, C₁₋₆alkoxy, or C₁₋₆ alkoxycarbonyl,

R^(10a), R^(10b), R^(10c), R^(10d), R^(10e), R^(10f), R^(10g), R^(10g2),R^(10h), R^(10h2), R^(10i), R^(10i2), R^(10j), R^(11a), R^(11b),R^(11c), R^(11d), R^(11e), R^(11f), R^(11f2), R^(11g), R^(11h),R^(11h2), R^(11i), R^(12a), R^(12b), R^(12c), R^(15a), R^(15b), R^(15c),R^(15d), R^(15e), R^(15e2), R^(15f), R^(15f2), R^(15g), R^(15h),R^(16a), R^(16b), R^(16c), R^(16d), R^(16e), R^(16e2), R^(16f), R^(16g),R^(17a), and R^(17b) are each independently the same or differenthydrogen atom, C₁₋₆ alkyl (the C₁₋₆ alkyl is optionally substituted with1 to 3 same or different substituents selected from a hydroxyl group,cyano group, C₁₋₆ alkoxy, and —NR^(18a)R^(18b)), or C₁₋₆ alkoxycarbonyl,and

R^(18a) and R^(18b) are each independently the same or differenthydrogen atom or C₁₋₆ alkyl.

In an exemplary embodiment, hydrogen of any hydroxy group in substituentgroups α2 and β2 is optionally substituted with a protecting group.

Examples of more preferred substituents used when “optionallysubstituted” herein include the following substituents.

Substituent group α3 more preferably includes

-   1) halogen atom-   2) hydroxyl group-   3) cyano group-   4) C₁₋₆ alkyl-   5) C₁₋₆ alkoxy-   6) C₁₋₆ alkylthio-   7) C₁₋₆ alkylcarbonyl    (however, each substituent from 4) to 7) is optionally substituted    with 1 to 5 same or different substituents selected from substituent    group (33)-   8) C₃₋₁₀ alicyclic group-   9) 5- to 6-membered heteroaryloxy-   10) 4- to 10-membered non-aryl heterocyclyloxy-   11) 5- to 6-membered heteroarylthio-   12) 4- to 10-membered non-aryl heterocyclylthio-   13) C₆₋₁₀ aryl-   14) 5- to 6-membered heteroaryl-   15) 4- to 10-membered non-aryl heterocycle    (however, each substituent from 8) to 15) is optionally substituted    with 1 to 5 substituents in substituent group β3 or 1) C₁₋₆ alkyl)-   16) —NR^(10a)R^(11a)-   17) —NR^(11b)—C(═O)R^(10b)-   18) —NR^(12a)—C(═O)NR^(10c)R^(11c)-   19) —C(═O)NR^(10d)R^(11d)-   20) —C(═NR^(13a))R^(10e)-   21) —C(═NR^(13b))NR^(10f)R^(11e)-   22) —NR^(11f)—C(═NR^(13c))R^(10g), and-   23) —NR^(12b)—C(═NR^(13d))—NR^(10h)R^(11g), and

substituent group β3 is more preferably

-   1) halogen atom,-   2) hydroxyl group,-   3) cyano group,-   4) —NR^(15a)R^(16a),-   5) —NR^(15b)—C(═O)R^(16b),-   6) —NR^(17a)—C(═O)NR^(15c)R^(16c),-   7) —C(═O)NR^(15d)R^(16d),-   8) —C(═NR^(13e))R^(15e),-   9) —C(═NR^(13f))NR^(15f)R^(16e),-   10) —NR^(16f)—C(═NR^(13g))R^(15g),and-   11) —NR^(17b)—C(═NR^(13h))—NR^(15h)R^(16g), wherein

R^(13a), R^(13a2), R^(13b), R^(13b2), R^(13c), R^(13d), R^(13e),R^(13e2), R^(13f), R^(13f2), R^(13g), and R^(13h) are each independentlythe same or different hydrogen atom, hydroxyl group, C₁₋₆ alkyl, C₁₋₆alkoxy, or C₁₋₆ alkoxycarbonyl,

R^(10a), R^(10b), R^(10c), R^(10d), R^(10e), R^(10f), R^(10e2),R^(10f2), R^(10g), R^(10h), R^(11a), R^(11b), R^(11c), R^(11d), R^(11e),R^(11e2), R^(11f), R^(11g), R^(12a), R^(12b), R^(15a), R^(15b), R^(15c),R^(15d), R^(15e), R^(15e2), R^(15f), R^(15f2), R^(15g), R^(15h),R^(16a), R^(16b), R^(16c), R^(16d), R^(16e), R^(16e2), R^(16f), R^(16g),R^(17a), and R^(17b) are each independently the same or differenthydrogen atom, C₁₋₆ alkyl (the C₁₋₆ alkyl is optionally substituted with1 to 3 same or different substituents selected from hydroxyl group,cyano group, C₁₋₆ alkoxy, and —NR^(18a)R^(18b)), or C₁₋₆ alkoxycarbonyl,and

R^(18a), and R^(18b) are each independently the same or differenthydrogen atom or C₁₋₆ alkyl.

In an exemplary embodiment, hydrogen of any hydroxyl group insubstituent groups α3 and β3 is optionally substituted with a protectinggroup.

In an exemplary embodiment, a hydroxyl group in the aforementionedsubstituent group (e.g., α (α1 or the like) β (β1 or the like), or I toVI) is also optionally substituted with a protecting group. In anexemplary embodiment, an amino group in substituent groups I to VI isalso optionally protected with a nitrogen protecting group.

As used herein, “C₁₋₆” means that the number of carbon atoms is 1 to 6.The same applies to other numbers. For example, “C₁₋₄” means that thenumber of carbon atoms is 1 to 4, and “C₁₋₃” means that the number ofcarbon atoms is 1 to 3. A description with a limitation in the number ofcarbons herein is only a preferred numerical range. It is intended sothat groups with a substituent with a number of carbons other than thenumber of carbons specified in the present disclosure are also withinthe scope of the present disclosure.

As used herein, “hydrocarbon group” is also referred to as a hydrocarbylgroup, referring to a group generated by removing at least one hydrogenfrom “hydrocarbon” comprising at least one carbon and at least onehydrogen.

As used herein, “functional group” refers to any group conferring sometype of functionality, encompassing a carboxyl group, nitrile group,carbonyl group, hydroxyl group, amino group, imino group, nitro group,halogen group, as well as alkyl group, and more broadly acid anhydridesand groups formed by a bond such as an ester bond, amide bond, or etherbond.

As used herein, “heteroatom” refers to atoms other than carbon atoms andhydrogen atoms such as oxygen atoms, nitrogen atoms, and sulfur atoms. Agroup comprising a heteroatom is also known as a hetero . . . group(e.g., heteroaryl group (means that an aryl group comprises at least aheteroatom) or heterocyclic group (means that a cyclic group (carbonring group) comprises at least one heteroatom)) or the like.

As used herein, “halogen atom” is an atom belonging to the halogengroup, referring to a fluorine atom, chlorine atom, bromine atom, iodineatom, or the like, and is preferably a fluorine atom or chlorine atom,and still more preferably a fluorine atom. A “halogen atom” is alsoreferred to as “halogen” or “halo”.

As used herein, “hydroxyl group” is a monovalent group of —OH. Thisgroup is also referred to as a “hydroxy group” or “hydroxy”.

As used herein, “carboxyl group” is a monovalent group of —COOH. Thisgroup is also referred to as a “carboxy group”, “carboxy”, or“carboxyl”.

As used herein, “cyano group” is a monovalent group of —CN.

As used herein, “amino” is a monovalent group of —NH₂. This group isalso referred to as an “amino group”.

As used herein, “alkyl” refers to a linear or branched saturatedaliphatic hydrocarbon group. “C₁₋₁₂ alkyl” is an alkyl group with 1 to12 carbon atoms. Examples thereof include, but are not limited to, C₁₋₆alkyl, heptyl, isoheptyl, octyl, isooctyl, nonyl, isnonyl, decyl,isodecyl, undecyl, isoundecyl, dodecyl, isododecy, and the like. “C₁₋₆alkyl” is an alkyl group with 1 to 6 carbon atoms, which is preferably“C₁₋₄ alkyl”, more preferably “C₁₋₃ alkyl”, and stil more preferably“C₁₋₂ alkyl”. Specific examples of “C₁₋₄ alkyl” include methyl, ethyl,propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and thelike. Specific examples of “C₁₋₆ alkyl” include, but are not limited to,C₁₋₄ alkyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1,2-dimethylpropyl, n-hexyl, and the like.

As used herein, “alkenyl” refers to a linear or branched unsaturatedaliphatic hydrocarbon group comprising at least one carbon-carbon doublebond. “C₂₋₁₂ alkenyl” is an alkenyl group with 2 to 12 carbon atoms.Examples thereof include, but are not limited to, heptenyl, isoheptenyl,octenyl, isooctenyl, nonenyl, isononenyl, decenyl, isodecenyl,undecenyl, isoundecenyl, dodecenyl, isododecenyl, and the like. “C₂₋₆alkenyl” is an alkenyl group with 2 to 6 carbon atoms. Preferredexamples thereof include “C₂₋₄ alkenyl”. Specific examples of “C₂₋₆alkenyl” include, but are not limited to, vinyl, 1-propenyl, 2-propenyl,1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl,2-methyl-2-propenyl, and the like.

As used herein, “alkynyl” refers to a linear or branched unsaturatedaliphatic hydrocarbon group comprising at least one carbon-carbon triplebond. “C₂₋₁₂ alkynyl” is an alkynyl group with 2 to 12 carbon atoms.Examples thereof include, but are not limited to, heptynyl, isoheptynyl,octynyl, isooctynyl, nonynyl, isononynyl, decynyl, isodecynyl,undecynyl, isoundecynyl, dodecynyl, isododecynyl, and the like. “C₂₋₆alkynyl” is an alkynyl group with 2 to 6 carbon atoms. Preferredexamples thereof include “C₂₋₄ alkynyl”. Specific examples of “C₂₋₆alkynyl” include, but are not limited to, ethynyl, 1-propynyl,2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 3-butynyl, 1-pentynyl,1-hexynyl, and the like.

As used herein, “aryl” refers to a monovalent group of a monocyclic orbicyclic aromatic hydrocarbon ring. “C₆₋₁₀ aryl” refers to an aryl groupwith 6 to 10 carbon atoms. Examples of “aryl” include, but are notlimited to, C₆ aryl, C₁₀ aryl, and the like. Specific examples of C₆aryl include, but are not limited to, phenyl and the like. Specificexamples of C₁₀ aryl include, but are not limited to, 1-naphthyl,2-naphthyl, and the like.

An aryl group as a substituent or a portion thereof may be fused to analicyclic group. For example, a phenyl group may be fused to acyclohexane ring to form a 1,2,3,4-tetrahydronaphthalenyl group. In sucha case, one of the possible carbon atoms on a benzene ring attaches tothe backbone, or to a group near the backbone, or to its atom. An arylgroup encompasses 5,6,7,8-tetrahydronaphthalen-1-yl and 5,6,7,8-tetrahydronaphthalen-2-yl.

As used herein, “arylalkyl” refers to alkyl substituted with at leastone aryl. “C₆₋₁₀ aryl C₁₋₆ alkyl” refers to C₁₋₆ alkyl substituted withat least one C₆₋₁₀ aryl. Specific examples of C₆₋₁₀ aryl C₁₋₆ alkylinclude, but are not limited to, benzyl(phenyl-CH₂—),phenethyl(phenyl-CH₂CH₂—), naphthalen-1-ylmethyl, naphthalen-2-ylmethyl,2-(naphthalen-1-yl)ethyl, 2-(naphthalen-2-yl)ethyl, and the like.

As used herein, “(optionally substituted amino)-arylalkyl” refers toarylalkyl substituted with an optionally substituted amino group,wherein the alkyl group, the aryl group, or both is substituted with anamino group. An amino group of such an arylalkyl group may beunsubstituted, or substituted with 1, 2, or 3 substituents, such asoptionally substituted alkyl (e.g., unsubstituted C₁₋₆ alkyl, C₃₋₆cycloalkyl-C₁₋₆ alkyl, C₃₋₆ cycloalkylcarbonyl, or the like). Examplesof (optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆ alkyl include, but arenot limited to, (di(alkyl)amino)benzyl, ((cycloalkylalkyl)amino)benzyl,((cycloalkylcarbonyl)amino)benzyl,((carbamoylalkyl)carbonylamino)benzyl,((carboxyalkyl)carbonyl)aminobenzyl, (di(alkyl)amino)naphthalenylmethyl,((cycloalkylalkyl)amino)naphthalenylmethyl,((cycloalkylcarbonyl)amino)naphthalenylmethyl,((carbamoylalkyl)carbonylamino)naphthalenylmethyl,((carboxyalkyl)carbonyl)aminonaphthalenylmethyl, and the like.

As used herein, the aryl moiety of “arylthio” is defined the same as theaforementioned aryl. Preferred examples of “C₆₋₁₀ arylthio” include “C₆or C₁₀ arylthio”. Specific examples of “C₆₋₁₀ aryloxy” include, but arenot limited to, phenylthio, 1-naphthylthio, 2-naphthylthio, and thelike.

As used herein, “aryl sulfonyl” refers to sulfonyl substituted with theaforementioned “aryl”. “C₆₋₁₀ aryl sulfonyl” is preferably “C₆ or C₁₀aryl sulfonyl”. Specific examples of “C₆₋₁₀ aryl sulfonyl” include, butare not limited to, phenylsulfonyl, 1-naphthylsulfonyl,2-naphthylsulfonyl, and the like.

As used herein, “heteroaryl” refers to a monovalent group of amonocyclic or bicyclic aromatic heterocycle comprising 1 to 4 same ordifferent heteroatoms selected from the group consisting of an oxygenatom, nitrogen atom, and sulfur atom.

As used herein, “5- to 6-membered heteroaryl” refers to a monovalentgroup of a monocyclic aromatic heterocycle consisting 5 to 6 atoms,comprising 1 to 4 same or different heteroatoms selected from the groupconsisting of an oxygen atom, nitrogen atom, and sulfur atom. Specificexamples of “5- to 6-membered heteroaryl” include, but are not limitedto, pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, oxazolyl,isooxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl,tetrazolyl, pyridyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, and thelike.

As used herein, “5- to 10-membered heteroaryl” refers to a monovalentgroup of a monocyclic or bicyclic aromatic heterocycle consisting of 5to 10 atoms, comprising 1 to 4 same or different heteroatoms selectedfrom the group consisting of an oxygen atom, nitrogen atom, and sulfuratom. Specific examples of “5- to 10-membered heteroaryl” include, butare not limited to, 5- to 6-membered heteroaryl, quinolyl, isoquinolyl,naphthyridinyl, quinoxalinyl, cinnolinyl, quinazolinyl, phthalazinyl,imidazopyridyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl,benzooxazolyl, benzoimidazolyl, indolyl, isoindolyl, indazolyl,pyrrolopyridyl, thienopyridyl, furopyridyl, benzothiadiazolyl,benzooxadiazolyl, pyridopyrimidinyl, benzofuryl, benzothienyl,benzo[1,3]dioxole, thienofuryl, chromenyl, chromanyl, coumarinyl,quinolonyl, and the like.

As used herein, “heteroarylalkyl” refers to alkyl substituted with atleast one heteroaryl. “5- to 10-membered heteroaryl C₁₋₆ alkyl” refersto C₁₋₆ alkyl substituted with at least one 5- to 10-memberedheteroaryl. Specific examples of 5- to 10-membered heteroaryl C₁₋₆ alkylinclude, but are not limited to, pyridin-2-ylmethyl, pyridin-4-ylmethyl,2-(quinolin-8-yl)ethyl, 2-(quinolin-5-yl)ethyl,2-(quinoxalin-5-yl)ethyl, 2-(1H-indol-3-yl)ethyl, and the like.

As used herein, “alicyclic group” refers to a monovalent group of amonocyclic , bicyclic, or tricyclic non-aromatic hydrocarbon ring,including those that have a partially unsaturated bond, those that havea partially crosslinked structure, those that are partially a spiro, andthose having 1, 2, or more carbonyl structures. An “alicyclic group”encompasses cycloalkyl, cycloalkenyl, and cycloalkynyl. “C₃₋₂₀ alicyclicgroup” is preferably a “C₃₋₁₀ alicyclic group”, more preferably a “C₃₋₆alicyclic group”. Specific examples of “C₃₋₂₀ alicyclic group” include,but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, cyclohexadinyl, cycloheptadinyl,cyclooctadinyl, adamantyl, norbornyl, and the like.

An alicyclic group can be a fused ring between a non-aryl ring and anaryl and/or heteroaryl ring. For example, cycloalkyl fused with C₆₋₁₀aryl or 5- to 6-membered heteroaryl is encompassed by an alicyclicgroup. Examples of fused alicyclic groups include a monovalent groupwith one hydrogen atom removed from 1,2,3,4-tetrahydronaphthalene,indane, 1,2,3,4-tetrahydroanthracene, and 5,6,7,8-tetrahydroquinoline.Specific examples thereof include 1,2,3,4-tetrahydronaphthalen-1-yl,1,2,3,4-tetrahydronaphthalen-2-yl, indan-1-yl, indan-2-yl,5,6,7,8-tetrahydroquinolin-5-yl, 5,6,7,8-tetrahydroquinolin-6-yl, andthe like. A fused alicyclic group attaches from any one of the possiblecyclic structure atoms on a non-aryl ring to the backbone.

As used herein, “C₃₋₁₀ alicyclic group” refers to a substituent with“C₃₋₁₀ alicyclic group” that is a monovalent group among theaforementioned “C₃₋₂₀ alicyclic group”.

As used herein, “alicyclic oxy” refers to an (alicyclic group)-O— group,and the alicyclic moiety is defined the same as an alicyclic group.“C₃₋₆ alicyclic oxy” refers to a (C₃₋₆ alicyclic group)-O— group, andthe C₃₋₆ alicyclic moiety is defined the same as a C₃₋₆ alicyclic group.“C₃₋₆ alicyclic oxy” is preferably “C₃₋₅ alicyclic oxy”. Specificexamples of “C₃₋₆ alicyclic oxy” include, but are not limited to,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, and thelike.

As used herein, “alicyclic carbonyl” refers to carbonyl substituted withthe “alicyclic group” described above. “C₃₋₁₀ alicyclic carbonyl” ispreferably “C₃₋₆ alicyclic carbonyl”. Specific examples of “C₃₋₁₀alicyclic carbonyl” include, but are not limited to,cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, and the like.

As used herein, “alicyclic thio” refers to an (alicyclic group)-S—group, and the alicyclic moiety is defined the same as above. “C₃₋₁₀alicyclic thio” is preferably “C₃₋₆ alicyclic thio”. Specific examplesof “C₃₋₆ alicyclic thio” include, but are not limited to,cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, andthe like.

As used herein, “alicyclic sulfonyl” refers to a sulfonyl groupsubstituted with the “alicyclic group” described above. “C₃₋₁₀ alicyclicsulfonyl” is preferably “C₃₋₆ alicyclic sulfonyl”. Specific examples of“C₃₋₁₀ alicyclic sulfonyl” include, but are not limited to,cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl,cyclohexylsulfonyl, and the like.

As used herein, “cycloalkyl” refers to a non-aromatic saturatedhydrocarbon ring group, including those that have a partiallycrosslinked structure, those that are partially spiro, those having 1,2, or more carbonyl structures. “C₃₋₂₀ cycloalkyl” refers to monocyclicor bicyclic cycloalkyl with 3 to 20 carbon atoms. “C₃₋₆ cycloalkyl”refers to monocyclic cycloalkyl with 3 to 6 carbon atoms. Specificexamples of C₃₋₆ cycloalkyl include, but are not limited to,cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

A cycloalkyl group can be fused to aryl and/or heteroaryl ring as asubstituent or a portion thereof. For example, a cyclohexyl group can befused to a benzene ring to form a 1,2,3,4-tetrahydronaphthalenyl group.In such a case, one of the possible carbon atoms on the cyclohexane ringattaches to the backbone, to a group near the backbone, or to its atom.A cycloalkyl group encompasses 1,2,3,4-tetrahydronaphthalen-1-yl,1,2,3,4-tetrahydronaphthalen-2-yl, indan-1-yl, indan-2-yl,5,6,7,8-tetrahydroquinolin-5-yl, and 5,6,7,8-tetrahydroquinolin-6-yl.

As used herein, “cycloalkylalkyl” refers to alkyl substituted with atleast one cycloalkyl. “C₃₋₆ cycloalkyl C₁₋₆ alkyl” refers to C₁₋₆ alkylsubstituted with at least one C₃₋₆ cycloalkyl. Specific examples of C₃₋₆cycloalkyl C₁₋₆ alkyl include, but are not limited to,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, 2-cyclopropylethyl, 2-cyclobutylethyl,2-cyclopentylethyl, 2-cyclohexylethyl, 3-cyclopropylpropyl,3-cyclobutylpropyl, 3-cyclopentylpropyl, 3-cyclohexylpropyl, and thelike.

As used herein, “heterocycloalkyl” refers to a non-aromatic saturated orpartially unsaturated heterocycle comprised of 3 or more atoms,copmrising 1, 2, or more same or different heteroatoms selected from thegroup consisting of an oxygen atom, nitrogen atom, and sulfur atom,including those that have a partially crosslinked structure and thosethat are partially spiro. “Heterocycloalkyl” encompasses “non-arylheterocycle”. Heterocycloalkyl can have a structure where a non-aromaticheterocycle is fused to an aryl ring and/or heteroaryl ring.

As used herein, “non-aryl heterocycle” refers to a monocyclic orbicyclic non-aromatic heterocycle comprised of 3 or more atoms,comprising 1, 2, or more same or different heteroatoms selected from thegroup consisting of an oxygen atom, nitrogen atom, and sulfur atom,including saturated non-aryl heterocycles, those that have a partiallyunsaturated attachment, those that have a partially crosslinkedstructure, and those that are partially spiro. A non-aryl heterocyclecan form a fused ring with aryl or heteroaryl. For example, a non-arylheterocycle fused to C₆₋₁₀ aryl or 5- to 6-membered heteroaryl is alsoencompassed by a heterocycle. 1, 2, or more carbonyl, thiocarbonyl,sulfinyl, or sulfonyl can be comprised to constitute the non-arylheterocycle. For example, lactam, thiolactam, lactone, thiolactone,cyclic imide, cyclic carbamate, cyclic thiocarbamate, and other cyclicgroups are also encompassed by the non-aryl heterocycle. In this regard,an oxygen atom of carbonyl, sulfinyl, and sulfonyl and a sulfur atom ofthiocarbonyl are not included in the number of members of the ring (ringsize) or the number of heteroatoms constituting the ring.

As used herein, “4- to 10-membered non-aryl heterocycle” refers to asubstituent with “4- to 10-membered non-aryl heterocycle” that is amonovalent group among the “non-aryl heterocycle” described above.

As used herein, the non-aryl heterocycle moiety of “non-arylheterocyclyloxy” is defined the same as the “non-aryl heterocycle”described above. “4- to 10-membered non-aryl heterocyclyloxy” ispreferably “4- to 6-membered non-aryl heterocyclyloxy”. Specificexamples of “4- to 10-membered non-aryl heterocyclyloxy” include, butare not limited to, tetrahydrofuranyloxy, tetrahydropyranyloxy,azetidinyloxy, pyrrolidinyloxy, piperidinyloxy, and the like.

As used herein, the non-aryl heterocycle moiety of “non-arylheterocyclylthio” is defined the same as the “non-aryl heterocycle”described above. “4- to 10-membered non-aryl heterocyclylthio” ispreferably “4- to 6-membered non-aryl heterocyclylthio”. Specificexamples of “4- to 10-membered non-aryl heterocyclylthio” include, butare not limited to, tetrahydropyranylthio, piperidinylthio, and thelike.

As used herein, “non-aryl heterocyclylcarbonyl” refers to a carbonylgroup substituted with the “non-aryl heterocycle” described above. “4-to 10-membered non-aryl heterocyclylcarbonyl” is preferably “4- to6-membered non-aryl heterocyclylcarbonyl”. Specific examples of “4- to10-membered non-aryl heterocyclylcarbonyl” include, but are not limitedto, azetidinylcarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl,morpholinylcarbonyl, and the like.

As used herein, “non-aryl heterocyclylsulfonyl” refers to a sulfonylgroup substituted with the “non-aryl heterocycle” described above. “4-to 10-membered non-aryl heterocyclylsulfonyl” is preferably “4- to6-membered non-aryl heterocyclylsulfonyl”. Specific examples of “4- to10-membered non-aryl heterocyclylsulfonyl” include, but are not limitedto, azetidinylsulfonyl, pyrrolidinylsulfonyl, piperidinylsulfonyl,morpholinylsulfonyl, and the like.

As used herein, “5- to 6-membered heterocycloalkyl” refers toheterocycloalkyl comprised of 5 to 6 cyclic atoms, comprising 1 or moresame or different heteroatoms selected from the group consisting of anoxygen atom, nitrogen atom, and sulfur atom.

As used herein, “heterocycloalkylalkyl” refers to alkyl substituted withat least one heterocycloalkyl.

As used herein, “alkylcarbonyl” is a monovalent group of —C(═O)-alkyl.Preferred examples of alkylcarbonyl include C₁₋₆ alkylcarbonyl. Specificexamples of C₁₋₆ alkylcarbonyl include, but are not limited to, acetyl(CH₃C(═O)—), n-propanoyl (CH₃CH₂C(═O)—), n-butanoyl (CH₃CH₂CH₂C(═O)—),n-pentanoyl (CH₃(CH₂)₃C(═O)—), n-hexanoyl (CH₃(CH₂)₄C(═O)—), n-heptanoyl(CH₃(CH₂)₅C(═O)—), and the like.

As used herein, “alkoxy” is a monovalent group of —O-alkyl. Preferredexamples of alkoxy include C₁₋₆ alkoxy (i.e., C₁₋₆ alkyl-O—), C₁₋₄alkoxy (i.e., C₁₋₄ alkyl-O—), and the like. Specific examples of C₁₋₄alkoxy include methoxy (CH₃O—), ethoxy (CH₃CH₂O—), n-propoxy(CH₃(CH₂)₂O—), isopropoxy ((CH₃)₂CHO—), n-butoxy (CH₃(CH₂)₃O—),isobutoxy ((CH₃)₂CHCH₂O—), tert-butoxy ((CH₃)₃CO—), sec-butoxy(CH₃CH₂CH(CH₃)O—), and the like. Specific examples of C₁₋₆ alkoxyinclude, but are not limited to, C₁₋₄ alkoxy, n-pentyloxy (CH₃(CH₂)₄O—),isopentyloxy ((CH₃)₂CHCH₂CH₂O—), neopentyloxy ((CH₃)₃CCH₂O—),tert-pentyloxy (CH₃CH₂C(CH₃)₂O—), 1,2-dimethylpropoxy(CH₃CH(CH₃)CH(CH₃)O—), and the like.

As used herein, “alkoxycarbonyl” is a monovalent group of—C(═O)—O-alkyl. Examples of alkoxycarbonyl include, but are not limitedto, C₁₋₆ alkoxycarbonyl, preferably C₁₋₄ alkoxycarbony. Specificexamples of C₁₋₄ alkoxycarbonyl include methoxycarbonyl, ethoxycarbonyl,n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,sec-butoxycarbonyl, tert-butoxycarbonyl, isobutoxycarbonyl, and thelike. Specific examples of C₁₋₆ alkoxycarbonyl include, but are notlimited to, C₁₋₄ alkoxycarbonyl, n-pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl,1,2-dimethylpropyloxycarbonyl, n-hexyl oxycarbonyl, and the like.

As used herein, “alkoxycarbonylamino” is a monovalent group of—NH—C(═O)—O-alkyl. Examples of alkoxycarbonylamino include, but are notlimited to, C₁₋₆ alkoxycarbonylamino, preferably C₁₋₄alkoxycarbonylamino. Specific examples of C₁₋₄ alkoxycarbonylaminoinclude methoxycarbonylamino, ethoxycarbonylamino,n-propoxycarbonylamino, isopropoxycarbonylamino, n-butoxycarbonylamino,sec-butoxycarbonylamino, tert-butoxycarbonylamino,isobutoxycarbonylamino, and the like. Specific examples of C₁₋₆alkoxycarbonylamino include, but are not limited to, C₁₋₄alkoxycarbonylamino, n-pentyloxycarbonylamino,isopentyloxycarbonylamino, neopentyloxycarbonylamino,tert-pentyloxycarbonylamino, 1,2-dimethylpropyloxycarbonylamino,n-hexyloxycarbonylamino, and the like.

As used herein, “haloalkyl” is a monovalent group of halogenated alkyl,having one or more hydrogen on an alkyl group substituted with halogen.The term “perhaloalkyl” refers to haloalkyl with all hydrogen on thealkyl group substituted with halogen. For example, perfluoroethyl is—CF₂CF₃, and perchloro-n-propyl is —CCl₂CCl₂CCl₃. Examples of haloalkylinclude C₁₋₆ haloalkyl, C₁₋₄ haloalkyl, C₁₋₃ haloalkyl, and the like.Specific examples of C₁₋₃ alkyl include, but are not limited to,fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl,dibromomethyl, trifluoromethyl, trichloromethyl, tribromomethyl,fluorochloromethyl, difluorochloromethyl, fluorodichloromethyl,fluoroethyl, chloroethyl, bromoethyl, trifluoroethyl, trichloroethyl,tribromoethyl, perfluoroethyl, perchloroethyl, perbromoethyl,perfluoropropyl, perchloropropyl, perbromopropyl, perfluoroisopropyl,perchloroisopropyl, perbromoisopropyl, and the like. Specific examplesof C₁₋₄ alkyl include, but are not limited to, C₁₋₃ haloalkyl,perfluorobutyl, perchlorobutyl, perbromobutyl, perfluoroisobutyl,perfluoro-t-butyl, and the like. Specific examples of C₁₋₆ alkylinclude, but are not limited to, C₁₋₄ haloalkyl, perfluoro-n-pentyl,perfluoroi sopentyl, perfluoroneopentyl, perfluorotert-pentyl,perfluoro-1,2-dimethylpropyl, and the like.

As used herein, “haloalkoxy” as well as “haloalkyloxy” is a monovalentgroup of —O-haloalkyl with one or more hydrogen on the alkyl group substitututed with halogen. The term “perhaloalkoxy” refers to haloalkoxywith all hydrogen on the alkyl group substituted with halogen. Forexample, perfluoroethoxy is —OCF₂CF₃, and perchloro-n-propoxy is—OCCl₂CCl₂CCl₃. Preferred examples of haloalkoxy include C₁₋₆haloalkoxy, C₁₋₄ haloalkoxy, C₁₋₃ haloalkoxy, and the like. Specificexamples of C₁₋₃ alkoxy include, but are not limited to, fluoromethoxy,chloromethoxy, bromomethoxy, difluoromethoxy, dichloromethoxy,dibromomethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy,fluorochloromethoxy, difluorochloromethoxy, fluorodichloromethoxy,fluoroethoxy, chloroethoxy, bromoethoxy, trifluoroethoxy,trichloroethoxy, tribromoethoxy, perfluoroethoxy, perchloroethoxy,perbromoethoxy, perfluoropropoxy, perchloropropoxy, perbromopropoxy,perfluoroisopropoxy, perchloroisopropoxy, perbromoisopropoxy, and thelike. Specific examples of C₁₋₄ alkoxy include, but are not limited to,C₁₋₃ haloalkoxy, perfluorobutoxy, perchlorobutoxy, perbromobutoxy,perfluoroisobutoxy, perfluoro-t-butoxy, and the like. Specific examplesof C₁₋₆ alkoxy include, but are not limited to, C₁₋₄ haloalkoxy,perfluoro-n-pentyloxy, perfluoroisopentyloxy, perfluoroneopentyloxy,perfluorotert-pentyloxy, perfluoro-1,2-dimethylpropoxy, and the like.

As used herein, “alkylsulfonyl” refers to a sulfonyl group substitutedwith the “alkyl” described above. “C₁₋₆ alkylsulfonyl” is preferably“C₁₋₄ alkylsulfonyl”. Specific examples of “C₁₋₆ alkylsulfonyl” include,but are not limited to, methylsulfonyl, propionylsulfonyl,butyrylsulfonyl, and the like.

As used herein, the alkyl moiety of “alkylthio” is defined the same asthe alkyl described above. Examples of “C₁₋₆ alkylthio” include “C₁₋₄alkylthio”, and preferred examples thereof include “C₁₋₃ alkylthio”.Specific examples of “C₁₋₆ alkylthio” include, but are not limited to,methylthio, ethylthio, propylthio, butylthio, isopropylthio,isobutylthio, tert-butylthio, sec-butylthio, isopentylthio,neopentylthio, tert-pentylthio, 1,2-dimethylpropylthio, and the like.

As used herein, “arylcarbonyl” is a monovalent group of —C(═O)-aryl.Preferred examples of arylcarbonyl include C₆₋₁₀ arylcarbonyl. Specificexamples of C₆₋₁₀ arylcarbonyl include, but are not limited to, benzoyl(i.e., phenyl-C(═O)—), 1-naphthylcarbonyl, 2-naphthylcarbonyl, and thelike.

As used herein, the aryl moiety of “aryloxy” is defined the same as thearyl described above. Preferred examples of “C₆₋₁₀ aryloxy” include “C₆or C₁₀ aryloxy”. Specific examples of “C₆₋₁₀ aryloxy group” include, butare not limited to, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxygroup, and the like.

As used herein, “heteroarylcarbonyl” is a monovalent group of—C(═O)-heteroaryl.

As used herein, “heteroarylcarbonyl group” refers to a carbonyl groupsubstituted with the “heteroaryl” described above. Specific examples of“5- to 6-membered heteroarylcarbonyl group” include, but are not limitedto, pyrazoylcarbonyl group, triazoylcarbonyl group, thiazoylcarbonylgroup, thiadiazoylcarbonyl group, pyridylcarbonyl group,pyridazoylcarbonyl group, and the like.

As used herein, the heteroaryl moiety of the “heteroaryloxy group” isdefined the same as the “heteroaryl” described above. The 5- to6-membered heteroaryl moiety of the “5- to 6-membered heteroaryloxygroup” is defined the same as “5-membered heteroaryl” or “6-memberedheteroaryl”, respectively. Specific examples of “5- to 6-memberedheteroaryloxy group” include, but are not limited to, a pyrazoyloxygroup, triazoyloxy group, thiazoyloxy group, thiadiazoyloxy group,pyridyloxy group, pyridazoyloxy group, and the like.

As used herein, the heteroaryl moiety of a “heteroarylthio group” isdefined the same as the “heteroaryl” described above. The 5- to6-membered heteroaryl moiety of “5- to 6-membered heteroarylthio group”is defined the same as “5-membered heteroaryl” or “6-memberedheteroaryl”, respectively. Specific examples of “5- to 6-memberedheteroarylthio group” include, but are not limited to, pyrazoylthiogroup, triazoylthio group, thiazoylthio group, thiadiazoylthio group,pyridylthio group, pyridazoylthio group, and the like.

As used herein, the heteroaryl moiety of a “heteroarylsulfonyl group” isdefined the same as the “heteroaryl” described above. A “5- to6-membered heteroarylsulfonyl group” refers to a sulfonyl groupsubstituted with a “5- to 6-membered heteroaryl”. Specific examples of“5- to 6-membered heteroarylsulfonyl group” include, but are not limitedto, pyrazoylsulfonyl group, triazoylsulfonyl group, thiazoylsulfonylgroup, thiadiazoylsulfonyl group, pyridylsulfonyl group,pyridazoylsulfonyl group, and the like.

As used herein, “acyl” refers to a monovalent group of —C(═O)—R_(acyl),wherein R_(acyl) is hydrogen, optionally substituted alkyl, optionallysubstituted alkenyl, optionally substituted alkynyl, optionallysubstituted aryl, optionally substituted heteroaryl, or optionallysubstituted heterocycloalkyl. Specific examples of acyl include, but arenot limited to, formyl, groups exemplified as alkylcarbonyl,arylcarbonyl, and heteroarylcarbonyl, and the like.

As used herein, “optionally substituted carbonyl” group refers to amonovalent group of —C(═O)— (hydrogen or any group selected from asubstituent group described herein). Examples of “optionally substitutedcarbonyl” group include, but are not limited to, formyl, and optionallysubstituted carbamoyl, alkylcarbonyl, alkoxycarbonyl, alkenylcarbonyl,alkenyloxycarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, arylcarbonyl,aryloxycarbonyl, cycloalkylcarbonyl, cycloalkyloxycarbonyl,heteroarylcarbonyl, heteroaryloxycarbonyl, heterocycloalkylcarbonyl,heterocycloalkyloxycarbonyl, and the like. A carbonyl group substitutedwith hydrogen is a formyl group. A carbonyl group substituted with aminois a carbamoyl group.

As used herein, “optionally substituted oxy” group refers to amonovalent group of —O— (hydrogen or any group selected from asubstituent group described herein). Examples of “optionally substitutedoxy” group include, but are not limited to, hydroxy, and optionallysubstituted alkyloxy, alkenyloxy, alkynyloxy, aryloxy, heteroaryloxy,heterocycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy,heterocycloalkylcarbonyloxy, and the like. An oxy group substituted withhydrogen is a hydroxy group.

As used herein, “carbamoyl” is a monovalent group of —C(═O)—NH₂.

As used herein, “amidinoamino” is a monovalent group of —NH—C(═NH)—NH₂.

As used herein, the phrase “a substituent-substituted group” means thatthe group is substituted with at least one substituent. For example,“hydroxy-substituted C₁₋₆ alkyl” refers to C₁₋₆ alkyl that has at leastone hydroxy substitution.

As used herein, “carbamoyl-substituted C₁₋₆ alkyl” is C₁₋₆ alkylsubstituted with at least one —C(═O)—NH₂ group. Examples of“carbamoyl-substituted C₁₋₆ alkyl” include, but are not limited to,carbamoyl-substituted C₁₋₄ alkyl. Specific examples of“carbamoyl-substituted C₁₋₄ alkyl” include, but are not limited to,2-amino-2-oxoethyl (i.e., H₂NC(═O)—CH₂— or carbamoylmethyl),3-amino-3-oxopropyl (i.e., H₂NC(═O)—CH₂CH₂— or carbamoylethyl),4-amino-4-oxobutyl (i.e., H₂NC(═O)—(CH₂)₃— or carbamoylpropyl),5-amino-5-oxopentyl (i.e., H₂NC(═O)—(CH₂)₄— or carbamoylbutyl), and thelike. Specific examples of “carbamoyl-substituted C₁₋₆ alkyl” include,but are not limited to, carbamoyl-substituted C₁₋₄ alkyl,6-amino-6-oxohexyl (i.e., H₂NC(═O)—(CH₂)₅— or carbamoylpentyl),7-amino-7-oxoheptyl (i.e., H₂NC(═O)—(CH₂)₆— or carbamoylhexyl), and thelike.

As used herein, “amidinoamino-substituted alkyl” or“guanidino-substituted alkyl” is alkyl substituted with at least one—NH—C(═NH)—NH₂ group, wherein the nitrogen atom of the amidinoaminogroup can be protected with a nitrogen protecting group (e.g.,tert-butoxycarbonyl group). Examples of “amidinoamino-substituted C₁₋₆alkyl” include, but are not limited to, “amidinoamino-substituted C₁₋₄alkyl” and the like. Specific examples of “amidinoamino-substituted C₁₋₄alkyl” include, but are not limited to, (amidinoamino)methyl,2-(amidinoamino)ethyl, 3-(amidinoamino)propyl, 4-(amidinoamino)butyl,and the like. Specific examples of “amidinoamino-substituted C₁₋₆ alkyl”include, but are not limited to, amidinoamino-substituted C₁₋₄ alkyl,5-(amidinoamino)pentyl, 6-(amidinoamino)hexyl, and the like. Examples ofamidinoamino groups protected with a nitrogen protecting group include

As used herein, “amidinoamino” is synonymous with “guanidino”.

As used herein, “carboxy-substituted alkyl” is alkyl substituted with atleast one —COOH group. Examples of “carboxy-substituted C₁₋₆ alkyl”include, but are not limited to, “carboxy-substituted C₁₋₄ alkyl” andthe like. Specific examples of “carboxy-substituted C₁₋₄ alkyl” include,but are not limited to, carboxymethyl, 2-carboxyethyl, 3-carboxypropyl,4-carboxybutyl, and the like. Specific examples of “carboxy-substitutedC₁₋₆ alkyl” include, but are not limited to, carboxy-substituted C₁₋₄alkyl, 5-carboxypentyl, 6-carboxyhexyl, and the like.

A “protecting group” refers to a group of atoms that blocks, reduces, orprevents reactivity of a functional group when attached to a reactivefunctional group in a molecule. The compound of the present disclosurecan have a substitution with a protecting group when appropriate orneeded at any of R₁ to R₄ or any position of a substituent thereof orother substituents or the like. Compounds comprising such a protectinggroup are also within the scope of the present disclosure. Typically, aprotecting group can be selectively removed during a synthesis processif desired. Examples of protecting groups are found in Greene and Wuts,Protective Groups in Organic Chemistry, 5th Edition, 2014, John Wiley &Sons, NY and Harrison et al., Compendium of Synthetic Organic Methods,Vol. 1 to 8, John Wiley & Sons, NY, or the like. As used herein, a“protecting group” can fall under the definitions for 1) to 53) ofsubstituent α and 1) to 26) of substituent β. In such a case, “54)protecting group” can be described as “54) protecting group otherthan 1) to 53)” in substituent group α1, and “27) protecting group” canbe described as “protecting group other than 1) to 26)” in substituentgroup β1. Representative examples of nitrogen protecting groups include,but are not limited to, formyl, acetyl, trifluoroacetyl, benzyl,benzyloxycarbonyl (“CBZ”), tert-butoxycarbonyl (“Boc”), trimethylsilyl(“TMS”), 2-trimethylsilylethanesulfonyl (“TES”), trityl and substitutedtrityl group, allyloxycarbonyl, 9-fluorenylmethyloxycarbonyl (“FMOC”),nitro-veratryloxycarbonyl (“NVOC”), groups represented by “Protect”herein, and the like. Representative examples of hydroxyl protectinggroups include, but are not limited to, groups that acylate (esterify)or alkylate a hydroxyl group, such as benzyl and trityl ether, as wellas alkyl ether, tetrahydropyranyl ether, trialkylsilyl ether (e.g., TMS,triethylsilyl, t-butyldimethylsilyl (TBDMS), and triisopropylsilyl(TIPS)), alkyldiarylsilyl ether (e.g., t-butyldiphenylsilyl (TBDPS)),triarylsilyl ether (e.g., triphenylsilyl), glycol ether (e.g., ethyleneglycol ether, propylene glycol ether, and the like), and allyl ether.

An amino group of the compound of the present disclosure (e.g., aminogroup of the backbone, amino group as a substituent, amino group in asubstituent of said compound, or the like) can be protected with anitrogen protecting group or a group represented by “Protect”. An aminogroup in a substituent listed in a substituent group can be furtherprotected with a nitrogen protecting group or a group represented by“Protect”. A protected substituent can also be used as a substituent.

A hydroxy group of the compound of the present disclosure (e.g., hydroxygroup as a substituent, a hydroxy group in a substituent of saidcompound, a hydroxy group in a substituent group described above, or thelike) can also be protected with a protecting group of a hydroxy group.A hydroxy group in a sub stituent listed in a sub stituent group can befurther protected with a hydroxyl protecting group described herein. Aprotected substituent can also be used as a substituent.

Preferred Embodiments

The preferred embodiments of the present disclosure are describedhereinafter. It is understood that the embodiments provided hereinafterare provided for the better understanding of the present disclosure, sothat the scope of the present disclosure should not be limited by thefollowing descriptions. Thus, it is apparent that those skilled in theart can refer to the descriptions herein to make appropriatemodifications within the scope of the present disclosure. It is alsounderstood that the following embodiments of the present disclosure canbe used individually or as a combination.

(Compound and Composition of the Present Disclosure)

In one aspect, the compound of the present disclosure can be exemplifiedas a compound represented by formula XXIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₃, and R₄ are each independently hydrogen, optionally substitutedalkyl, optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkynyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

If one of R_(2A) or R_(2B) is hydrogen herein, it is understood that thesame definition as R₂ described herein can be used.

In another aspect, the compound of the present disclosure can beexemplified as a compound represented by formula XXIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein R₁, R_(2a), R_(2B), and R₃ are defined the same as those forformula XXIF described herein.

In still another aspect, the compound of the present disclosure can beexemplified as a compound represented by formula XXIIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein R₁, R_(2A), R_(2B), and R₃ are defined the same as those forformula XXIF described herein.

In still another aspect, the compound of the present disclosure can beexemplified as a compound represented by formula XXIIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein R₁, R₂, and R₃ are defined the same as those for formula XXIFdescribed herein.

In one embodiment, the alkyl, alkenyl, alkynyl, cycloalkyl,heterocycloalkyl, aryl, heteroaryl, and carbonyl of R₁, R₃, and ifpresent R₄ are each independently and optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from substituent group I, and the alkyl, alkenyl, alkynyl,cycloalkyl, heterocycloalkyl, aryl, heteroaryl, carbonyl, and thenon-aryl heterocycle and the heteroaryl ring of R_(2A) and R_(2B) areeach independently and optionally substituted with one to the maximumsubstitutable number of the same or different sub stituents selectedfrom sub stituent group I.

In one embodiment, R₁, R₃, and if present R₄ are each independentlyhydrogen, optionally substituted alkyl, optionally substitutedcycloalkyl, optionally substituted heterocycloalkyl, optionallysubstituted aryl, optionally substituted heteroaryl, or optionallysubstituted carbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

In some cases for substituents in this embodiment, R_(2A) and R_(2B) areeach independently hydrogen, optionally substituted alkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl,optionally substituted aryl, or optionally substituted heteroaryl and/orR_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a non-aryl heterocycle, wherein the non-aryl heterocyclesare each independently and optionally substituted.

Alternatively, in another embodiment for (an imine form), R₁ and R₃ areeach independently hydrogen, optionally substituted alkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl,optionally substituted aryl, optionally substituted heteroaryl, oroptionally substituted carbonyl, and R_(2A) and R_(2B) are eachindependently hydrogen, optionally substituted alkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl,optionally substituted aryl, optionally substituted heteroaryl, oroptionally substituted carbonyl, or R_(2A) and R_(2B), together with thenitrogen atom to which they are attached, form a non-aryl heterocycle orheteroaryl ring, wherein the non-aryl heterocycle and the heteroarylring are each independently and optionally substituted.

In some cases, R₁ and R₃ are each independently hydrogen, optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, or optionallysubstituted heteroaryl, and R_(2A) and R_(2B) are each independentlyhydrogen, optionally substituted alkyl, optionally substitutedcycloalkyl, optionally substituted heterocycloalkyl, optionallysubstituted aryl, or optionally substituted heteroaryl, and/or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle, wherein the non-aryl heterocycles are eachindependently and optionally substituted.

In one embodiment, R₁, R₃, and if present R₄ are each independentlyhydrogen, optionally substituted C₁₋₁₂ alkyl, optionally substitutedC₃₋₁₀ cycloalkyl, optionally substituted 5- to 10-memberedheterocycloalkyl, optionally substituted C₆₋₁₀ aryl, optionallysubstituted 5- to 10-membered heteroaryl, or optionally substitutedcarbonyl, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₃₋₁₀ cycloalkyl,optionally substituted 5- to 10-membered heterocycloalkyl, optionallysubstituted C₆₋₁₀ aryl, optionally substituted 5- to 10-memberedheteroaryl, or optionally substituted carbonyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.

In some cases, R_(2A) and R_(2B) are each independently hydrogen,optionally substituted C₁₋₁₂ alkyl, optionally substituted C₃₋₁₀cycloalkyl, optionally substituted 5- to 10-membered heterocycloalkyl,optionally substituted C₆₋₁₀ aryl, or optionally substituted 5- to10-membered heteroaryl, and/or R_(2A) and R_(2B), together with thenitrogen atom to which they are attached, form a non-aryl heterocycle,wherein the non-aryl heterocycles are each independently and optionallysubstituted.

In one embodiment, R₁, R₃, and if present R₄ are each independentlyhydrogen, optionally substituted alkyl, optionally substitutedarylalkyl, optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, formyl, optionally substituted alkylcarbonyl,optionally substituted alkoxycarbonyl, optionally substitutedarylcarbonyl, optionally substituted aryloxycarbonyl, optionallysubstituted heteroarylcarbonyl, optionally substitutedheteroaryloxycarbonyl, optionally substituted cycloalkylcarbonyl,optionally substituted cycloalkyloxycarbonyl, optionally substitutedheterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁, R₃, and R₄ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group II,and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl, formyl,optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, optionally substituted heteroarylcarbonyl,optionally substituted heteroaryloxycarbonyl, optionally substitutedcycloalkylcarbonyl, optionally substituted cycloalkyloxycarbonyl,optionally substituted heterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R_(2A) and R_(2B) areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group II,or R_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a 5- to 6-membered non-aryl heterocycle or heteroarylring, wherein the non-aryl heterocycle and the heteroaryl ring areoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from sub stituent group II.

In one embodiment, R₁, R₃, and if present R₄ are each independentlyhydrogen, optionally substituted C₁₋₁₂ alkyl, optionally substitutedC₆₋₁₀ aryl C₁₋₁₂ alkyl, optionally substituted C₃₋₁₀ cycloalkyl,optionally substituted 5- to 10-membered heterocycloalkyl, formyl,optionally substituted C₁₋₁₂ alkylcarbonyl, optionally substituted C₁₋₁₂alkoxycarbonyl, optionally substituted C₆₋₁₀ arylcarbonyl, optionallysubstituted C₆₋₁₀ aryloxycarbonyl, optionally substituted 5- to10-membered heteroarylcarbonyl, optionally substituted 5- to 10-memberedheteroaryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R₁, R₃, andR₄ are optionally substituted with one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup III, and

R_(2A) and R_(2B) are each independently hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl,optionally substituted C₃₋₁₀ cycloalkyl, optionally substituted 5- to10-membered heterocycloalkyl, formyl, optionally substituted C₁₋₁₂alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl, optionallysubstituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted 5- to 10-memberedheteroarylcarbonyl, optionally substituted 5- to 10-memberedheteroaryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R_(2A) andR_(2B) are optionally substituted with one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup III, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a 5- to 6-membered non-aryl heterocycle,wherein the non-aryl heterocycle is optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from substituent group V.

In some cases, R_(2A) and R_(2B) are each independently hydrogen,optionally substituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ arylC₁₋₁₂ alkyl, optionally substituted C₃₋₁₀ cycloalkyl, optionallysubstituted 5- to 10-membered heterocycloalkyl, or formyl, wherein thegroups of R_(2A) and R_(2B) are optionally substituted with one to themaximum substitutable number of the same or different substituentsselected from substituent group III.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,optionally substituted alkyl, optionally substituted arylalkyl,optionally substituted cycloalkyl, formyl, optionally substitutedalkylcarbonyl, optionally substituted alkoxycarbonyl, optionallysubstituted arylcarbonyl, optionally substituted aryloxycarbonyl,optionally substituted cycloalkylcarbonyl, optionally substitutedcycloalkyloxycarbonyl, optionally substituted heterocycloalkylcarbonyl,optionally substituted heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted alkylcarbamoyl, optionally substitutedalkoxycarbamoyl, optionally substituted arylcarbamoyl, optionallysubstituted heteroarylcarbamoyl, optionally substitutedcycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₄ areoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from sub stituent groupIII.

In some cases, R₁ and if present R₄ are each independently hydrogen,optionally substituted alkyl, optionally substituted arylalkyl,optionally substituted cycloalkyl, or formyl, wherein the groups of R₁and R₄ are optionally substituted with one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup III.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,optionally substituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ arylC₁₋₁₂ alkyl, optionally substituted C₃₋₁₀ cycloalkyl, formyl, optionallysubstituted C₁₋₁₂ alkylcarbonyl, optionally substituted C₁₋₁₂alkoxycarbonyl, optionally substituted C₆₋₁₀ arylcarbonyl, optionallysubstituted C₆₋₁₀ aryloxycarbonyl, optionally substituted C₃₋₁₀cycloalkylcarbonyl, optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl,optionally substituted 5- to 10-membered heterocycloalkylcarbonyl,optionally substituted 5- to 10-membered heterocycloalkyloxycarbonyl,carbamoyl, optionally substituted C₁₋₁₂ alkylcarbamoyl, optionallysubstituted C₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀arylcarbamoyl, optionally substituted 5- to 10-memberedheteroarylcarbamoyl, optionally substituted C₃₋₁₀ cycloalkylcarbamoyl,or optionally substituted 5- to 10-membered heterocycloalkylcarbamoyl,wherein the groups of R₁ and R₄ are optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from substituent group III.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,optionally substituted alkyl, optionally substituted arylalkyl, formyl,optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, carbamoyl, or optionally substitutedalkylcarbamoyl, wherein the groups of R₁ and R₄ are optionallysubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from substituent group III.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,optionally substituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ arylC₁₋₁₂ alkyl, formyl, optionally substituted C₁₋₁₂ alkylcarbonyl,optionally substituted C₁₋₁₂ alkoxycarbonyl, optionally substitutedC₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀ aryloxycarbonyl,carbamoyl, or optionally substituted C₁₋₁₂ alkylcarbamoyl, wherein thegroups of R₁ and R₄ are optionally substituted with one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group III.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,alkyl, alkyl substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from the group consistingof amino, substituted amino, substituted oxy, substituted carbonyl,cycloalkyl, and substituted cycloalkyl, arylalkyl, arylalkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, alkyl,substituted alkyl, hydroxy, substituted oxy, amino, substituted amino,and nitro, formyl, substituted carbonyl, or substituted oxycarbonyl,wherein the substituted amino, substituted oxy, substituted alkyl,substituted carbonyl, substituted cycloalkyl, substituted carbonyl, andsubstituted oxycarbonyl in R₁ and R₄ each independently have one to themaximum substitutable number of the same or different substituentsselected from substituent group IV.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different sub stituents selectedfrom the group consisting of amino, substituted amino, substituted oxy,substituted carbonyl, C₃₋₁₀ cycloalkyl, and substituted C₃₋₁₀cycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, C₁₋₆ alkyl,substituted alkyl, hydroxy, substituted oxy, amino, substituted amino,and nitro, formyl, substituted carbonyl, or substituted oxycarbonyl,wherein the substituted amino, substituted oxy, substituted alkyl,substituted carbonyl, substituted cycloalkyl, substituted carbonyl, andsubstituted oxycarbonyl in R₁ and R₄ each independently have one to themaximum substitutable number of the same or different substituentsselected from substituent group IV.

In one embodiment, R₁ and R₃ are each independently hydrogen, optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted cycloalkyl, formyl, optionally substituted alkylcarbonyl,optionally substituted alkoxycarbonyl, optionally substitutedarylcarbonyl, optionally substituted aryloxycarbonyl, optionallysubstituted cycloalkylcarbonyl, optionally substitutedcycloalkyloxycarbonyl, optionally substituted heterocycloalkylcarbonyl,optionally substituted heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted alkylcarbamoyl, optionally substitutedalkoxycarbamoyl, optionally substituted arylcarbamoyl, optionallysubstituted heteroarylcarbamoyl, optionally substitutedcycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from substituent group III.

In one embodiment, and R3 are each independently hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl,optionally substituted C₃₋₁₀ cycloalkyl, formyl, optionally substitutedC₁₋₁₂ alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl,optionally substituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃are optionally substituted with one to the maximum substitutable numberof the same or different substituents selected from substituent groupIII.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,alkyl, alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofamidinoamino, alkoxy, alkoxycarbonyl, carbamoyl, carboxy, hydroxy, trialkylsilyloxy, and cycloalkyl, arylalkyl, arylalkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, alkyl,haloalkyl, alkoxy, haloalkoxy, amino, substituted amino, nitro, andhydroxy, formyl, alkylcarbonyl, arylalkylcarbonyl, arylalkyloxycarbonyl,alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, carbamoyl,alkylcarbamoyl, or arylalkylcarbamoyl, wherein the substituted aminoeach independently has one to the maximum substitutable number of thesame or different substituents selected from substituent group IV.

In one embodiment, R₁ and if present R₄ are each independently hydrogen,C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different sub stituents selectedfrom the group consisting of amidinoamino, C₁₋₆ alkoxy, C₁₋₆alkoxycarbonyl, carbamoyl, carboxy, hydroxy, tri-C₁₋₆ alkylsilyloxy, andC₃₋₁₀ cycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, amino,substituted amino, nitro, and hydroxy, formyl, C₁₋₁₂ alkylcarbonyl,C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl, C₆₋₁₀ aryl C₁₋₆ alkyloxycarbonyl, C₁₋₁₂alkoxycarbonyl, C₆₋₁₀ arylcarbonyl, C₆₋₁₀ aryloxycarbonyl, carbamoyl,C₁₋₁₂ alkylcarbamoyl, or C₆₋₁₀ aryl C₁₋₆ alkylcarbamoyl, wherein thesubstituted amino has one to the maximum substitutable number of thesame or different substituents selected from substituent group IV.

In one embodiment, R₁ and if present R₄ are each independently, C₁₋₁₂alkyl, C₁₋₁₂ alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of amidinoamino, C₁₋₆ alkoxycarbonyl-substitutedamidinoamino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, carbamoyl, carboxy,hydroxy, tri-C₁₋₆ alkylsilyloxy, and C₃₋₁₀ cycloalkyl, C₆₋₁₀ aryl C₁₋₆alkyl, or C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, amino, substituted amino, nitro, and hydroxy,wherein the substituted amino optionally has one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

In one embodiment, R₃ is hydrogen, alkyl, alkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of formyl, substituted carbonyl,hydroxy, substituted oxy, substituted carbonyl, amino, substitutedamino, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, andsubstituted heterocycloalkyl, arylalkyl, arylalkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, nitro,hydroxy, substituted oxy, amino, substituted amino, alkyl, andsubstituted alkyl, heteroarylalkyl, or substituted heteroarylalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substituted alkyl,and substituted heteroarylalkyl in R₃ each independently and optionallyhave one to the maximum substitutable number of the same or differentsubstituents selected from substituent group IV.

In some cases, R₃ is hydrogen, alkyl, alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of hydroxy, substituted oxy,substituted carbonyl, amino, substituted amino, cycloalkyl, substitutedcycloalkyl, heterocycloalkyl, and substituted heterocycloalkyl,arylalkyl, arylalkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of halogen, nitro, hydroxy, substituted oxy, amino,substituted amino, alkyl, and substituted alkyl, heteroarylalkyl, orsubstituted heteroarylalkyl, wherein the substituted oxy, substitutedamino, substituted cycloalkyl, substituted heterocycloalkyl, substitutedalkyl, and substituted heteroarylalkyl in R₃ each independently andoptionally have one to the maximum substitutable number of the same ordifferent substituents selected from substituent group IV.

In one embodiment, R₃ can be hydrogen, alkyl, formyl, alkylcarbonyl,arylalkylcarbonyl, alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of hydroxy, trialkylsilyloxy, alkoxy,alkoxycarbonyl, alkoxycarbonylamino, cycloalkyl, carboxy, amino,amidinoamino, alkoxycarbonyl-substituted amidinoamino, carbamoyl, andheterocycloalkyl, arylalkyl, arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,monoalkylamino, dialkylamino, alkyl, haloalkyl, alkoxy, haloalkoxy,carboxyalkylcarbonylamino, carbamoylalkylcarbonylamino,cycloalkylcarbonylamino, and cycloalkylalkylamino, heteroarylalkyl, oralkoxycarbonyl-substituted heteroarylalkyl.

In some cases, R₃ can be hydrogen, alkyl, alkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of hydroxy, trialkylsilyloxy, alkoxy,alkoxycarbonyl, alkoxycarbonylamino, cycloalkyl, carboxy, amino,amidinoamino, alkoxycarbonyl-substituted amidinoamino, carbamoyl, andheterocycloalkyl, arylalkyl, arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,monoalkylamino, dialkylamino, alkyl, haloalkyl, alkoxy, haloalkoxy,carboxyalkylcarbonylamino, carbamoylalkylcarbonylamino,cycloalkylcarbonylamino, and cycloalkylalkylamino, heteroarylalkyl, oralkoxycarbonyl-substituted heteroarylalkyl.

In one embodiment, R₃ can be hydrogen, C₁₋₁₂ alkyl, formyl, C₁₋₆alkylcarbonyl, C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl, C₁₋₁₂ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of hydroxy, tri-C₁₋₆alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₁₋₆alkoxycarbonylamino, C₃₋₆ cycloalkyl, carboxy, amino, amidinoamino, C₁₋₆alkoxycarbonyl-substituted amidinoamino, carbamoyl, and 5- to 6-memberedheterocycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, amino, mono-C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, carboxy C₁₋₆alkylcarbonylamino, carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino, 5- to10-membered heteroaryl C₁₋₆ alkyl, or C₁₋₆ alkoxycarbonyl-substituted 5-to 10-membered heteroaryl C₁₋₆ alkyl.

In some cases, R₃ can be hydrogen, C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of hydroxy, tri-C₁₋₆alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₁₋₆alkoxycarbonylamino, C₃₋₆ cycloalkyl, carboxy, amino, amidinoamino, C₁₋₆alkoxycarbonyl-substituted amidinoamino, carbamoyl, and 5- to 6-memberedheterocycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, amino, mono-C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, carboxy C₁₋₆alkylcarbonylamino, carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino, 5- to10-membered heteroaryl C₁₋₆ alkyl, or C₁₋₆ alkoxycarbonyl-substituted 5-to 10-membered heteroaryl C₁₋₆ alkyl.

In one embodiment, R₃ can be C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substituted withone to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of hydroxy, tri-C₁₋₆alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₁₋₆alkoxycarbonylamino, C₃₋₆ cycloalkyl, carboxy, amino, amidinoamino, C₁₋₆alkoxycarbonyl-substituted amidinoamino, carbamoyl, and 5- to 6-memberedheterocycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, or C₆₋₁₀ aryl C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, amino, mono-C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, carboxy C₁₋₆alkylcarbonylamino, carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino.

In one embodiment, R₃ is hydrogen, alkyl, alkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of amino, substituted amino, carboxy,substituted oxycarbonyl, carbamoyl, substituted aminocarbonyl, hydroxy,substituted oxy, cycloalkyl, and substituted cycloalkyl, arylalkyl, orarylalkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, alkyl, substituted alkyl, carboxy, substituted oxycarbonyl,hydroxy, and substituted oxy, wherein the substituted amino, substitutedoxy, substituted oxycarbonyl, substituted aminocarbonyl, substitutedalkyl, substituted cycloalkyl, substituted carbonyl, and substitutedoxycarbonyl in R3 each independently have one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

In one embodiment, R₃ is hydrogen, alkyl, alkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, alkoxycarbonyl,carbamoyl, carboxy, hydroxy, trialkylsilyloxy, amino,alkoxycarbonylamino, and cycloalkyl, arylalkyl, or arylalkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, alkyl,alkoxycarbonyl, and hydroxy.

In one embodiment, R₃ is hydrogen, C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino, C₁₋₆alkoxycarbonyl, carbamoyl, carboxy, hydroxy, tri-C₁₋₆ alkylsilyloxy,amino, C₁₋₆ alkoxycarbonylamino, and C₃₋₁₀ cycloalkyl, C₆₋₁₀ aryl C₁₋₆alkyl, or C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyl, andhydroxy.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,alkyl, alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting offormyl, substituted carbonyl, hydroxy, substituted oxy, amino,substituted amino, cycloalkyl, substituted cycloalkyl, heterocycloalkyl,and substituted heterocycloalkyl, arylalkyl, arylalkyl substituted withone to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, alkyl,substituted alkyl, hydroxy, and substituted oxy, heteroarylalkyl,substituted heteroarylalkyl, cycloalkyl, or substituted cycloalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substitutedheteroarylalkyl, and substituted alkyl in R_(2A) and R_(2B) eachindependently have one to the maximum substitutable number of the sameor different substituents selected from substituent group IV, or R_(2A)and R_(2B), together with the nitrogen atom to which they are attached,form a non-aryl heterocycle, wherein the non-aryl heterocycle isoptionally substituted with one or up to the maximum substitutablenumber of the same or different substituents selected from substituentgroup VI.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,alkyl, alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofamidinoamino, alkoxy, alkoxycarbonyl, carbamoyl, carboxy, hydroxy,amino, alkoxycarbonylamino, cycloalkyl, and heterocycloalkyl, arylalkyl,arylalkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, alkyl, haloalkyl, alkoxy, and hydroxy, heteroarylalkyl,alkoxycarbonyl-substituted heteroarylalkyl, or cycloalkyl, or R_(2A) andR_(2B), together with the nitrogen atom to which they are attached, forma 5- to 6-membered non-aryl heterocycle, wherein the non-arylheterocycle is optionally substituted with one or up to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group VI.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,C₁₋₁₂ alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofamidinoamino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, carbamoyl, carboxy,hydroxy, amino, C₁₋₆ alkoxycarbonylamino, C₃₋₁₀ cycloalkyl, and 5- to10-membered heterocycloalkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhalogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, and hydroxy, 5- to10-membered heteroaryl C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyl-substituted 5- to10-membered heteroaryl C₁₋₆ alkyl, or C₃₋₁₀ cycloalkyl, R_(2A) andR_(2B), together with the nitrogen atom to which they are attached, forma 5- to 6-membered non-aryl heterocycle, wherein the non-arylheterocycle is optionally substituted with one or up to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group VI.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,alkyl, alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting offormyl, substituted carbonyl, hydroxy, substituted oxy, substitutedcarbonyl, amino, substituted amino, cycloalkyl, substituted cycloalkyl,heterocycloalkyl, and substituted heterocycloalkyl, arylalkyl, arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, substituted oxy, amino, substituted amino, alkyl, andsubstituted alkyl, heteroarylalkyl, or substituted heteroarylalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substituted alkyl,and substituted heteroarylalkyl in R_(2A) and R_(2B) each independentlyhave one to the maximum substitutable number of the same or differentsubstituents selected from substituent group IV, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle, wherein the non-aryl heterocycle is optionallysubstituted with one or up to the maximum substitutable number of thesame or different substituents selected from substituent group VI.

In some cases, R_(2A) and R_(2B) are each independently hydrogen, alkyl,alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhydroxy, substituted oxy, substituted carbonyl, amino, substitutedamino, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, andsubstituted heterocycloalkyl, arylalkyl, arylalkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, nitro,hydroxy, substituted oxy, amino, substituted amino, alkyl, andsubstituted alkyl, heteroarylalkyl, or substituted heteroarylalkyl,wherein the substituted oxy, substituted amino, substituted cycloalkyl,substituted heterocycloalkyl, substituted alkyl, and substitutedheteroarylalkyl in R_(2A) and R_(2B) each independently have one to themaximum substitutable number of the same or different substituentsselected from substituent group IV, or R_(2A) and R_(2B), together withthe nitrogen atom to which they are attached, form a non-arylheterocycle, wherein the non-aryl heterocycle is optionally substitutedwith one or up to the maximum substitutable number of the same ordifferent substituents selected from substituent group VI.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,alkyl, alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting offormyl, alkylcarbonyl, arylalkylcarbonyl, hydroxy, tri alkyl silyloxy,alkoxy, alkoxycarbonyl, alkoxycarbonylamino, cycloalkyl, carboxy, amino,amidinoamino, alkoxycarbonyl-substituted amidinoamino, carbamoyl, andheterocycloalkyl, arylalkyl, arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,monoalkylamino, dialkylamino, alkyl, haloalkyl, alkoxy,carboxyalkylcarbonylamino, carbamoylalkylcarbonylamino,cycloalkylcarbonylamino, and cycloalkylalkylamino, heteroarylalkyl, oralkoxycarbonyl-substituted heteroarylalkyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle, wherein the non-aryl heterocycle is optionallysubstituted with one or up to the maximum substitutable number of thesame or different substituents selected from substituent group VI.

In some cases, R_(2A) and R_(2B) are each independently hydrogen, alkyl,alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofhydroxy, trialkylsilyloxy, alkoxy, alkoxycarbonylamino, cycloalkyl,carboxy, amino, amidinoamino, alkoxycarbonyl-substituted amidinoamino,and heterocycloalkyl, arylalkyl, arylalkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,monoalkylamino, dialkylamino, alkyl, haloalkyl, alkoxy,carboxyalkylcarbonylamino, carbamoylalkylcarbonylamino,cycloalkylcarbonylamino, and cycloalkylalkylamino, heteroarylalkyl, oralkoxycarbonyl-substituted heteroarylalkyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle, wherein the non-aryl heterocycle is optionallysubstituted with one or up to the maximum substitutable number of thesame or different substituents selected from substituent group VI.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of formyl, C₁₋₆ alkylcarbonyl, C₆₋₁₀ aryl C₁₋₆alkylcarbonyl, hydroxy, tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆alkoxycarbonyl, C₁₋₆ alkoxycarbonylamino, C₃₋₁₀ cycloalkyl, carboxy,amino, amidinoamino, C₁₋₆ alkoxycarbonyl-substituted amidinoamino,carbamoyl, and 5- to 6-membered heterocycloalkyl, C₆₋₁₀ aryl C₁₋₁₂alkyl, C₆₋₁₀ aryl C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, nitro, hydroxy, amino, mono-C₁₋₆alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy,carboxy C₁₋₆ alkylcarbonylamino, carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino, 5- to10-membered heteroaryl C₁₋₁₂ alkyl, or C₁₋₆ alkoxycarbonyl-substituted5- to 10-membered heteroaryl C₁₋₁₂ alkyl, or R_(2A) and R_(2B), togetherwith the nitrogen atom to which they are attached, form a 5- to6-membered non-aryl heterocycle, wherein the non-aryl heterocycle isoptionally substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consting ofhalogen, nitro, hydroxy, amino, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy,C₁₋₆ alkoxycarbonyl, C₃₋₆ cycloalkylcarbonylamino, and C₃₋₆ cycloalkylC₁₋₆ alkylamino.

In some cases, R_(2A) and R_(2B) are each independently hydrogen, C₁₋₁₂alkyl, C₁₋₁₂ alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of hydroxy, tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy, C₁₋₆alkoxycarbonylamino, C₃₋₁₀ cycloalkyl, carboxy, amino, amidinoamino,C₁₋₆ alkoxycarbonyl-substituted amidinoamino, and 5- to 6-memberedheterocycloalkyl, C₆₋₁₀ aryl C₁₋₁₂ alkyl, C₆₋₁₀ aryl C₁₋₁₂ alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, amino, mono-C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, carboxy C₁₋₆ alkylcarbonylamino,carbamoyl C₁₋₆ alkylcarbonylamino, C₃₋₆ cycloalkylcarbonylamino, andC₃₋₆ cycloalkyl C₁₋₆ alkylamino, 5- to 10-membered heteroaryl C₁₋₁₂alkyl, or C₁₋₆ alkoxycarbonyl-substituted 5- to 10-membered heteroarylC₁₋₁₂ alkyl, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a 5- to 6-membered non-aryl heterocycle,wherein the non-aryl heterocycle is optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino.

In one embodiment, R_(2A) and R_(2B) are each independently hydrogen,C₁₋₁₂ alkyl, C₁₋₁₂ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of hydroxy, tri-C₁₋₆ alkylsilyloxy, C₁₋₆ alkoxy,C₁₋₆ alkoxycarbonyl, C₁₋₆ alkoxycarbonylamino, C₃₋₁₀ cycloalkyl,carboxy, amino, amidinoamino, C₁₋₆ alkoxycarbonyl-substitutedamidinoamino, carbamoyl, and 5- to 6-membered heterocycloalkyl, C₆₋₁₀aryl C₁₋₁₂ alkyl, C₆₋₁₀ aryl C₁₋₁₂ alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, nitro, hydroxy, amino,mono-C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkyl, C₁₋₆ haloalkyl,C₁₋₆ 6 alkoxy, carboxy C₁₋₆ alkylcarbonylamino, carbamoyl C₁₋₆alkylcarbonylamino, C₃₋₆ cycloalkylcarbonylamino, and C₃₋₆ cycloalkylC₁₋₆ alkylamino, 5- to 10-membered heteroaryl C₁₋₁₂ alkyl, or C₁₋₆alkoxycarbonyl-substituted 5- to 10-membered heteroaryl C₁₋₁₂ alkyl, orR_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a 5- to 6-membered non-aryl heterocycle, wherein thenon-aryl heterocycle is optionally substituted with one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group consisting of halogen, nitro, hydroxy, amino, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl, C₃₋₆cycloalkylcarbonylamino, and C₃₋₆ cycloalkyl C₁₋₆ alkylamino.

In one embodiment, R₁ is alkyl; alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, carbamoyl, carboxy,hydroxy, and cycloalkyl; arylalkyl; or arylalkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of halogen, alkyl, haloalkyl, alkoxy,substituted amino, and hydroxy, wherein the substituted amino has one tothe maximum substitutable number of the same or different substituentsselected from substituent group IV. Alternatively, R₁ is alkyl;arylalkyl; or arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, alkyl, haloalkyl, alkoxy, substitutedamino, and hydroxy, wherein the substituted amino has one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group IV.

In one embodiment, R₁ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino,carbamoyl, carboxy, hydroxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆alkyl; or C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, substituted amino, and hydroxy, wherein the substituted aminohas one to the maximum substitutable number of the same or differentsubstituents selected from substituent group IV. Alternatively, R₁ isC₁₋₁₂ alkyl; C₆₋₁₀ aryl C₁₋₆ alkyl; or C₆₋₁₀ aryl C₁₋₆ alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of halogen, C₁₋₆ alkyl,C₁₋₆ haloalkyl, C₁₋₆ alkoxy, substituted amino, and hydroxy, wherein thesubstituted amino has one to the maximum substitutable number of thesame or different substituents selected from substituent group IV.

In one embodiment, R_(2A) is hydrogen, and R_(2B) is alkyl; alkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting ofamidinoamino, carbamoyl, carboxy, hydroxy, and cycloalkyl; arylalkyl;arylalkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, alkyl, haloalkyl, alkoxy, and hydroxy; or cycloalkyl.Alternatively, R_(2A) is hydrogen, and R_(2B) is alkyl; arylalkyl;arylalkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofhalogen, alkyl, haloalkyl, alkoxy, and hydroxy; or cycloalkyl.

In one embodiment, R_(2A) is hydrogen, and R_(2B) is C₁₋₁₂ alkyl; C₁₋₁₂alkyl substituted with one to the maximum substitutable number of thesame or different substituents selected from the group consisting ofamidinoamino, carbamoyl, carboxy, hydroxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀aryl C₁₋₆ alkyl; C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of halogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, and hydroxy; or C₃₋₁₀ cycloalkyl. Alternatively,R_(2A) is hydrogen, and R_(2B) is C₁₋₁₂ alkyl; C₆₋₁₀ aryl C₁₋₆ alkyl;C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, andhydroxy; or C₃₋₁₀ cycloalkyl.

In one embodiment, R₃ is alkyl; alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino, carbamoyl, carboxy,hydroxy, and cycloalkyl; arylalkyl; or arylalkyl substituted with one tothe maximum substitutable number of the same or different substituentsselected from the group consisting of alkyl and hydroxy. Alternatively,R₃ is alkyl or arylalkyl.

In one embodiment, R₃ is C₁₋₁₂ alkyl; C₁₋₁₂ alkyl substituted with oneto the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino,carbamoyl, carboxy, hydroxy, and C₃₋₁₀ cycloalkyl; C₆₋₁₀ aryl C₁₋₆alkyl; or C₆₋₁₀ aryl C₁₋₆ alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of C₁₋₆ alkyl and hydroxy. Alternatively, in oneembodiment, R₃ is C₁₋₁₂ alkyl or C₆₋₁₀ aryl C₁₋₆ alkyl.

In one embodiment, R₄ is hydrogen, alkyl, alkylcarbonyl,arylalkylcarbonyl, arylalkyloxycarbonyl, alkoxycarbonyl, carbamoyl, orarylalkylcarbamoyl.

In one embodiment, R₄ is hydrogen, C₁₋₁₂ alkyl, C₁₋₁₂ alkylcarbonyl,C₆₋₁₀ aryl C₁₋₆ alkylcarbonyl, C₆₋₁₀ aryl C₁₋₆ alkyloxycarbonyl, C₁₋₁₂alkoxycarbonyl, carbamoyl, or C₆₋₁₀ aryl C₁₋₆ alkylcarbamoyl.

In one embodiment, R₁ is hydrogen, methyl, ethyl, isobutyl, isopentyl,amidinoaminopropyl, tert-butoxyethyl, tert-butoxypropyl,(tert-butoxycarbonyl)ethyl, carbamoyl methyl, carboxyethyl,hydroxyethyl, hydroxypropyl, cyclopentylmethyl, cyclohexylmethyl,benzyl, phenylethyl, naphthalenylmethyl, fluorobenzyl, chlorobenzyl,dichlorobenzyl, methylbenzyl, tert-butylbenzyl, (trifluoromethyl)benzyl,methoxybenzyl, ethoxybenzyl, tert-butoxybenzyl, aminobenzyl,(cyclopentylcarbonylamino)benzyl, (cyclopentylmethylamino)benzyl,(dimethylamino)benzyl, (carbamoylethylcarbonylamino)benzyl,(carboxyethylcarbonylamino)benzyl, nitrobenzyl, hydroxybenzyl,3-methylbutanoyl, isobutylcarbonyl, 2-phenylacetyl,isopropyloxycarbonyl, benzoyl, or phenyloxycarbonyl.

In another embodiment, R₁ is methyl, n-propyl, isobutyl, isopentyl,amidinoaminopropyl, tert-butoxycarbonyl-sub stituted amidinoaminopropyl,tert-butoxyethyl, tert-butoxypropyl, (tert-butoxycarbonyl)ethyl,carboxyethyl, hydroxyethyl, hydroxypropyl, aminopropyl,2-(tert-butyl-dimethyl silyloxy)ethyl, cyclopentylmethyl,cyclohexylmethyl, benzyl, phenylethyl, naphthalenylmethyl, fluorobenzyl,chlorobenzyl, dichlorobenzyl, methylbenzyl, (tert-butyl)benzyl,methoxybenzyl, ethoxybenzyl, (tert-butoxy)benzyl,(trifluoromethoxy)benzyl, (dim ethylamino)benzyl, nitrobenzyl, orhydroxybenzyl.

In one embodiment, R_(2A) is hydrogen, and R_(2B) is methyl, isopropyl,isobutyl, n-pentyl, isopentyl, n-hexyl, heptyl, amidinoaminopropyl,tert-butoxyethyl, tert-butoxycarbonylmethyl, carbamoylmethyl,carbamoylethyl, carboxyethyl, hydroxyethyl, aminobutyl,((tert-butoxycarbonyl)amino)butyl, cyclohexylmethyl,(tetrahydro-2H-pyran-2-yl)m ethyl, benzyl, phenylethyl,naphthalenylmethyl, naphthalenylethyl, fluorobenzyl, chlorobenzyl,dichlorobenzyl, (fluorophenyl)ethyl, methylbenzyl,(trifluoromethyl)benzyl, methoxybenzyl, tert-butoxybenzyl,hydroxybenzyl, α-hydroxymethylphenethyl, P-hydroxyphenethyl,pyridinylmethyl, (1H-indol-3-yl)ethyl,(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, cyclopentyl, orcyclohexyl, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a pyrrolidine ring or piperidine ring.

In one embodiment, R_(2A) and R_(2B) are each independently isopropyl,isobutyl, sec-butyl, pentyl, isopentyl, n-hexyl, heptyl,amidinoaminopropyl, tert-butoxycarbonyl-substituted amidinoaminopropyl,tert-butoxyethyl, tert-butoxycarbonylmethyl,(tert-butoxycarbonyl)ethylcarbamoylethyl, carboxyethyl, hydroxyethyl,aminopropyl, aminobutyl, ((tert-butoxycarbonyl)amino)butyl,cyclopentylmethyl, cyclohexylmethyl,(1,2,3,4-tetrahydronaphthalenyl)methyl, (tetrahydro-2H-pyranyl)methyl,benzyl, phenylethyl, naphthalenylmethyl, (naphthalenyl)ethyl,P-hydroxyphenethyl, α-(hydroxymethyl)phenethyl, fluorobenzyl,chlorobenzyl, dichlorobenzyl, (fluorophenyl)ethyl, methylbenzyl,(trifluoromethyl)benzyl, methoxybenzyl, (tert-butoxy)benzyl,hydroxybenzyl, pyridinylmethyl, quinolinylethyl,(1-(tert-butoxycarbonyl)-1H-indolyl)ethyl, cyclopentyl, or cyclohexyl,or R_(2A) and R_(2B), together with the nitrogen atom to which they areattached, form a pyrrolidine ring or piperidine ring.

In one embodiment, R₃ is n-propyl, isobutyl, isopentyl,amidinoaminopropyl, (methoxycarbonyl)ethyl, (tert-butoxycarbonyl)ethyl,carbamoylmethyl, carboxyethyl, hydroxymethyl, hydroxyethyl, (tert-butyldi methyl silyloxy)ethyl, aminobutyl, ((tert-butoxycarbonyl)amino)butyl,cyclohexylmethyl, cyclohexylethyl, benzyl, phenylethyl, phenylpropyl,phenylbutyl, naphthalenylmethyl, naphthalenylethyl, chlorobenzyl,methylbenzyl, (m ethylphenyl)ethyl, (i sopropylphenyl)ethyl, orhydroxybenzyl.

In one embodiment, R₃ is n-propyl, isobutyl, isopentyl,amidinoaminopropyl, tert-butoxycarbonyl-substituted amidinoaminopropyl,(methoxycarbonyl)ethyl, (tert-butoxycarbonyl)ethyl, carboxyethyl,hydroxyethyl, aminopropyl, (tert-butyldimethylsilyloxy)ethyl,((tert-butoxycarbonyl)amino)butyl, cyclopentylmethyl, cyclohexylmethyl,cyclohexylethyl, benzyl, phenylethyl, phenylpropyl, phenylbutyl,naphthalenylmethyl, naphthalenylethyl, chlorobenzyl, methylbenzyl,(methylphenyl)ethyl, (isopropylphenyl)ethyl, (tert-butoxy)benzyl, orhydroxybenzyl.

In one embodiment, R₄ is hydrogen, methyl, ethyl, isobutyl, formyl,acetyl, 3-methylbutanoyl, 2-phenylacetyl, methoxycarbonyl,ethoxycarbonyl, 2-methylpropyloxycarbonyl, tert-butoxycarbonyl, benzoyl,benzyl, benzyloxycarbonyl, aminocarbonyl, N-benzylaminocarbonyl,propylcarbamoyl, N-isobutylaminocarbonyl, or N-benzylaminocarbonyl.

In some embodiments, the compound of the present disclosure can beexemplified as a compound represented by formula IF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein

R₁, R₂, and R₃ are each independently optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted arylalkyl, optionally substitutedheteroarylalkyl, optionally substituted cycloalkylalkyl, or optionallysubstituted heterocycloalkylalkyl, and

R₄ is hydrogen, optionally substituted alkyl, optionally substitutedalkenyl, optionally substituted alkynyl, optionally substitutedarylalkyl, optionally substituted heteroarylalkyl, optionallysubstituted cycloalkylalkyl, optionally substitutedheterocycloalkylalkyl, optionally substituted alkylcarbonyl, optionallysubstituted alkoxycarbonyl, optionally substituted arylcarbonyl,optionally substituted heteroarylcarbonyl, or optionally substitutedcarbamoyl.

In one embodiment, R₁, R₂, and R₃ are each independently optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted heteroarylalkyl, or optionally substituted cycloalkylalkyl.

In one embodiment, R₁, R₂, and R₃ are each independently optionallysubstituted C₁₋₆ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl,optionally substituted 5- to 10-membered heteroaryl C₁₋₆ alkyl, oroptionally substituted C₃₋₆ cycloalkyl C₁₋₆ alkyl.

In one embodiment, R₁, R₂, and R₃ are each independently optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted heteroarylalkyl, or optionally substituted cycloalkylalkyl,and R₄ is hydrogen, optionally substituted alkyl, optionally substitutedalkylcarbonyl, optionally substituted arylcarbonyl, optionallysubstituted alkoxycarbonyl, or optionally substituted alkylcarbamoyl.

In one embodiment, R₁, R₂, and R₃ are each independently C₁₋₆ alkyl,hydroxy-substituted C₁₋₆ alkyl, carbamoyl-substituted C₁₋₆ alkyl,amino-substituted C₁₋₆ alkyl, amidinoamino-substituted C₁₋₆ alkyl,carboxy-substituted C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄alkoxycarbonyl-substituted 5- to 10-membered heteroaryl C₁₋₆ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₆ alkyl, halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄alkoxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, (optionally substitutedamino)-C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted C₁₋₆alkyl, C₁₋₄ alkoxycarbonylamino-sub stituted C₁₋₆ alkyl, 5- to6-membered heterocycloalkyl-substituted C₁₋₆ alkyl, or C₃₋₆ cycloalkylC₁₋₆ alkyl.

In one embodiment, R₁, R₂, and R₃ are each independently C₁₋₆ alkyl,hydroxy-substituted C₁₋₆ alkyl, carbamoyl-substituted C₁₋₆ alkyl,amino-substituted C₁₋₆ alkyl, amidinoamino-substituted C₁₋₆ alkyl,carboxy-substituted C₁₋₆ alkyl, C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄alkoxycarbonyl-substituted 5- to 10-membered heteroaryl C₁₋₆ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₆ alkyl, halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄alkoxy-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, (optionally substitutedamino)-C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxycarbonyl-substituted C₁₋₆alkyl, C₁₋₄ alkoxycarbonylamino-substituted C₁₋₆ alkyl, 5- to 6-memberedheterocycloalkyl-substituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl C₁₋₆ alkyl.

In one embodiment, R₁, R₂, and R₃ are each independently alkyl oroptionally substituted arylalkyl.

In one embodiment, R₁, R₂, and R₃ are each independently C₁₋₆ alkyl oroptionally substituted C₆₋₁₀ aryl C₁₋₆ alkyl.

In one embodiment, R₁, R₂, and R₃ are each independently C₁₋₆ alkyl,C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ aryl C₁₋₆ alkyl,halogen-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₆ alkyl, or (optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆alkyl.

In one embodiment, R₁, R₂, and R₃ are each independently C₁₋₆ alkyl,C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ aryl C₁₋₆ alkyl,chloro-substituted C₆₋₁₀ aryl C₁₋₆ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₆ alkyl, or (optionally substituted amino)-C₆₋₁₀ aryl C₁₋₆alkyl.

In one embodiment, R₁ is C₁₋₆ alkyl or C₆ aryl C₁₋₄ alkyl, R₂ is C₁₋₆alkyl or C₁₋₄ alkyl-substituted benzyl, and R₃ is C₁₋₆ alkyl or C₆ arylC₁₋₄ alkyl.

In one embodiment, R₁ and R₃ are each independently alkyl or optionallysubstituted benzyl, and R₂ is optionally substituted benzyl.

In one embodiment, R₁ and R₃ are each independently C₁₋₆ alkyl, benzyl,C₁₋₄ alkyl-substituted benzyl, chloro-substituted benzyl, C₁₋₄alkoxy-substituted benzyl, or amino-substituted benzyl, and R₂ is benzylor chloro-substituted benzyl.

In one embodiment, R₁ and R₃ are each independently isobutyl, isopentyl,4-(dimethylamino)benzyl, 4-methylbenzyl, 4-methoxybenzyl,3-chlorobenzyl, 4-chlorobenzyl, or 3,4-dichlorobenzyl, and R₂ is benzyl,3-chlorobenzyl, or 3,4-dichlorobenzyl.

In one embodiment, R₁ is isobutyl, benzyl, 4-(dimethylamino)benzyl,4-methylbenzyl, 4-tert-butylbenzyl, 4-methoxybenzyl, 3-chlorobenzyl,4-chlorobenzyl, or 3,4-dichlorobenzyl, R₂ is isobutyl, benzyl,naphthalen-1-ylmethyl, 4-methylbenzyl, 4-chlorobenzyl, or3,4-dichlorobenzyl, and R₃ is isobutyl, isopentyl, or benzyl.

In one embodiment, R₁ is C₁₋₆ alkyl, hydroxy-substituted C₁₋₄ alkyl,carbamoyl-substituted C₁₋₄ alkyl, amino-substituted C₁₋₆ alkyl,amidinoamino-substituted C₁₋₄ alkyl, carboxy-substituted C₁₋₄ alkyl,C₁₋₄ alkoxycarbonyl-substituted C₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl,hydroxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀aryl C₁₋₄ alkyl, halo-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, or C₅₋₆cycloalkyl C₁₋₄ alkyl.

In one embodiment, R₁ is methyl, isopropyl, isobutyl, isopentyl,n-hexyl, 3-amino-3-oxopropyl, 3-(tert-butoxy)-3-oxopropyl, benzyl,naphthalen-1-ylmethyl, 2-carboxyethyl, carbamoylmethyl,3-(amidinoamino)propyl, 4-fluorobenzyl, 4-hydroxybenzyl,4-(tert-butoxy)benzyl, 3,4-dichlorobenzyl, naphthalen-1-ylmethyl,phenethyl, hydroxymethyl, 2-hydroxyethyl, or cyclohexylmethyl.

In one embodiment, R₁ is methyl, isopropyl, isobutyl, isopentyl,n-hexyl, 2-hydroxyethyl, carbamoylmethyl, 3-amino-3-oxopropyl,3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl,3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl, 3-(tert-butoxy)-3-oxopropyl,hydroxymethyl, cyclohexylmethyl, or

In one embodiment, R₁ is methyl, isobutyl, isopentyl,3-(tert-butoxy)-3-oxopropyl, benzyl, naphthalen-1-ylmethyl,4-hydroxybenzyl, 4-(tert-butoxy)benzyl, 3,4-dichlorobenzyl, orcyclohexylmethyl.

In one embodiment, R₁ is isopropyl, isobutyl, isopentyl, n-hexyl,cyclohexylmethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl, carbamoylmethyl,carbamoylethyl, 3-(amidinoamino)propyl, hydroxymethyl, or hydroxyethyl.

In one embodiment, R₁ is isobutyl, isopentyl, cyclohexylmethyl, benzyl,phenethyl, naphthalen-1-ylmethyl, 4-hydroxybenzyl, 4-fluorobenzyl,2-carboxyethyl, carbamoylmethyl, 3-(amidinoamino)propyl, orhydroxyethyl.

In one embodiment, R₁ is isobutyl, benzyl, 4-hydroxybenzyl,2-carboxyethyl, 3-(amidinoamino)propyl, or naphthalen-1-ylmethyl.

In one embodiment, R₁ is isobutyl, 3-(amidinoamino)propyl,2-carboxyethyl, benzyl, naphthalen-1-ylmethyl, 4-hydroxybenzyl,4-(tert-butoxy)benzyl, 3-(tert-butoxy)-3-oxopropyl, or

In one embodiment, R₁ is isobutyl, 3-hydroxypropyl, 3-amino-3-oxopropyl,6-aminohexyl, 2-carboxyethyl, benzyl, naphthalen-1-ylmethyl,4-hydroxybenzyl, or cyclohexylmethyl.

In one embodiment, R₂ is C₁₋₄ alkyl, hydroxy-substituted C₁₋₄ alkyl,carbamoyl-substituted C₁₋₄ alkyl, amino-substituted C₁₋₄ alkyl,amidinoamino-substituted C₁₋₄ alkyl, carboxy-substituted C₁₋₄ alkyl,C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄ alkoxycarbonyl-substituted 5- to 10-memberedheteroaryl C₁₋₄ alkyl, C₁₋₄ alkyl-substituted C₆₋₁₀ aryl C₁₋₄ alkyl,hydroxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, halogen-substituted C₆₋₁₀aryl C₁₋₄ alkyl, C₁₋₄ alkoxy-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkoxycarbonyl-substituted C₁₋₄ alkyl, C₁₋₄ alkoxycarbonylamino-substituted C₁₋₄ alkyl, 5- to 6-membered heterocycloalkyl-substituted C₁₋₄alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

In one embodiment, R₂ is naphthalen-1-ylmethyl or optionally substitutedbenzyl.

In one embodiment, R₂ is isopropyl, 1-methylpropyl, isobutyl, isopentyl,n-hexyl, hydroxymethyl, 2-hydroxyethyl, carbamoylmethyl,3-amino-3-oxopropyl, 3-(amidinoamino)propyl, 4-aminobutyl,2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,2-(naphthalen-1-yl)ethyl,2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 4-fluorobenzyl, 3-chlorobenzyl,4-chlorobenzyl, 3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl,2-(tert-butoxy)-2-oxoethyl, 4-((tert-butoxycarbonyl)amino)butyl,(tetrahydro-2H-pyran-2-yl)methyl, or cyclohexylmethyl.

In one embodiment, R₂ is isopropyl, 1-methylpropyl, isobutyl, isopentyl,n-hexyl, hydroxymethyl, 2-hydroxyethyl, carbamoylmethyl,3-amino-3-oxopropyl, 4-aminobutyl, 3-(amidinoamino)propyl,2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,2-naphthalen-1-yl)ethyl, 2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl,3-methylbenzyl, 4-methylbenzyl, 4-hydroxybenzyl, 4-fluorobenzyl,3-chlorobenzyl, 4-chlorobenzyl, 3,4-dichlorobenzyl,4-(tert-butoxy)benzyl, 2-(tert-butoxy)-2-oxoethyl,3-(tert-butoxy)-3-oxopropyl, 4-((tert-butoxycarbonyl)amino)butyl,(tetrahydro-2H-pyran-2-yl)methyl, cyclohexylmethyl, or

In one embodiment, R₂ is isobutyl, 2-hydroxyethyl, 3-amino-3-oxopropyl,4-aminobutyl, 2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,2-(naphthalen-1-yl)ethyl,2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl, 3-methylbenzyl,4-methylbenzyl, 4-hydroxybenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 3,4-dichlorobenzyl, 4-(tert-butoxy)benzyl, 2-(tert-butoxy)-2-oxoethyl,4-((tert-butoxycarbonyl)amino)butyl, (tetrahydro-2H-pyran-2-yl)methyl,or cyclohexylmethyl.

In one embodiment, R₂ is 1-methylpropyl, isopropyl, isobutyl, isopentyl,n-hexyl, benzyl, 4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl,carbamoylmethyl, carbamoylethyl, 3-(amidinoamino)propyl, hydroxymethyl,2-hydroxyethyl, phenethyl, naphthalen-1-ylmethyl, or cyclohexylmethyl.

In one embodiment, R₂ is isopropyl, 1-methylpropyl, isobutyl,3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, naphthalen-1-ylmethyl,4-hydroxybenzyl, 4-(tert-butoxy)benzyl, 3-(tert-butoxy)-3-oxopropyl, or

In one embodiment, R₂ is isopropyl, isobutyl, isopentyl, benzyl,4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl, carbamoylmethyl,3-(amidinoamino)propyl, hydroxyethyl, phenethyl, naphthalen-1-ylmethyl,or n-hexyl.

In one embodiment, R₂ is isobutyl, 2-hydroxyethyl, 3-amino-3-oxopropyl,4-aminobutyl, 2-carboxyethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,3-methylbenzyl, 4-methylbenzyl, 4-hydroxybenzyl, cyclohexylmethyl, or2-(1H-indol-3-yl)ethyl.

In one embodiment, R₂ is 1-methylpropyl, isopropyl, isobutyl, benzyl,4-hydroxybenzyl, 2-carboxyethyl, 3-(amidinoamino)propyl, ornaphthalen-1-ylmethyl.

In one embodiment, R₃ is C₁₋₄ alkyl, hydroxy-substituted C₁₋₄ alkyl,carbamoyl-substituted C₁₋₄ alkyl, C₁₋₄ alkoxycarbonyl-substituted C₁₋₄alkyl, amino-substituted C₁₋₄ alkyl, amidinoamino-substituted C₁₋₄alkyl, carboxy-substituted C₁₋₄ alkyl, C₆₋₁₀ aryl C₁₋₄ alkyl, C₁₋₄alkyl-substituted C₆₋₁₀ aryl C₁₋₄ alkyl, hydroxy-substituted C₆₋₁₀ arylC₁₋₄ alkyl, or C₅₋₆ cycloalkyl C₁₋₄ alkyl.

In one embodiment, R₃ is isopropyl, isobutyl, isopentyl, n-hexyl,3-amino-3-oxopropyl, 3-methoxy-3-oxopropyl, 4-aminobutyl,2-carboxyethyl, carbamoylmethyl, 3-(amidinoamino)propyl, benzyl,naphthalen-l-ylmethyl, phenethyl, hydroxymethyl, 2-hydroxyethyl,4-fluorobenzyl, 3-methylbenzyl, 4-methylbenzyl, 4-hydroxybenzyl,4-((tert-butoxycarbonyl)amino)butyl, or cyclohexylmethyl.

In one embodiment, R₃ is isopropyl, isobutyl, isopentyl, n-hexyl,hydroxymethyl, 2-hydroxyethyl, carbamoylmethyl, 3-amino-3-oxopropyl,4-aminobutyl, 3-(amidinoamino)propyl, 2-carboxyethyl, benzyl, phenethyl,naphthalen-1-ylmethyl, 3-methylbenzyl, 4-methylbenzyl, 4-hydroxybenzyl,4-fluorobenzyl, 4-(tert-butoxy)benzyl, 3-methoxy-3-oxopropyl,3-(tert-butoxy)-3-oxopropyl, 4-((tert-butoxycarbonyl)amino)butyl,cyclohexylmethyl, or

In one embodiment, R₃ is isobutyl, isopentyl, 3-amino-3-oxopropyl,3-methoxy-3-oxopropyl, 4-aminobutyl, 2-carboxyethyl, benzyl, phenethyl,3-methylbenzyl, 4-methylbenzyl, 4-hydroxybenzyl,4-((tert-butoxycarbonyl)amino)butyl, or cyclohexylmethyl.

In one embodiment, R₃ is isopropyl, isobutyl, isopentyl, n-hexyl,cyclohexylmethyl, benzyl, phenethyl, naphthalen-1-ylmethyl,4-hydroxybenzyl, 4-fluorobenzyl, 2-carboxyethyl, carbamoylmethyl,carbamoylethyl, 3-(amidinoamino)propyl, hydroxymethyl, or hydroxyethyl.

In one embodiment, R₃ is isobutyl, isopentyl, benzyl, phenethyl,4-hydroxybenzyl, 2-carboxyethyl, carbamoylmethyl,3-(amidinoamino)propyl, hydroxymethyl, or naphthalen-1-ylmethyl.

In one embodiment, R₃ is isobutyl, benzyl, 4-hydroxybenzyl,2-carboxyethyl, 3-(amidinoamino)propyl, or naphthalen-1-ylmethyl.

In one embodiment, R₃ is isobutyl, 2-carboxyethyl,3-(amidinoamino)propyl, benzyl, naphthalen-1-ylmethyl, 4-hydroxybenzyl,4-(tert-butoxy)benzyl, 3-(tert-butoxy)-3-oxopropyl, or

In one embodiment, R₃ is isobutyl, hydroxymethyl, 3-amino-3-oxopropyl,4-aminobutyl, 2-carboxyethyl, benzyl, 2-naphthylmethyl, 4-hydroxybenzyl,or cyclohexylmethyl.

In one embodiment, R₁ is C₁₋₆ alkyl or C₆₋₁₀ aryl C₁₋₆ alkyl, and R₂ andR₃ are each independently C₁₋₆ alkyl or optionally substituted C₆₋₁₀aryl C₁₋₆ alkyl.

In one embodiment, R₁ is isobutyl, isopentyl, or benzyl, R₂ is isobutyl,benzyl, phenethyl, 3-methylbenzyl, 4-methylbenzyl, or3,4-dichlorobenzyl, and R₃ is isobutyl, benzyl, phenethyl,3-methylbenzyl, or 4-methylbenzyl.

In one embodiment, R₁ is isobutyl, R₂ is benzyl, and R₃ is benzyl.

In one embodiment, R₁ is benzyl, R₂ is benzyl, and R₃ is isobutyl.

In one embodiment, R₁ is isobutyl, R₂ is benzyl, and R₃ is3-methylbenzyl.

In one embodiment, R₁ is benzyl, R₂ is 3,4-dichlorobenzyl, and R₃ isisobutyl.

In one embodiment, R₁ is isobutyl, R₂ is 4-methylbenzyl, and R₃ isbenzyl.

In one embodiment, R₁ is benzyl, R₂ is isobutyl, and R₃ is isobutyl.

In one embodiment, R₄ is hydrogen, optionally substituted alkyl,optionally substituted alkylcarbonyl, optionally substitutedarylcarbonyl, or optionally substituted alkoxycarbonyl.

In one embodiment, R₄ is hydrogen, optionally substituted C₁₋₆ alkyl,optionally substituted C₁₋₆ alkylcarbonyl, optionally substituted C₆₋₁₀arylcarbonyl, optionally substituted C₁₋₆ alkoxycarbonyl, or optionallysubstituted C₁₋₆ alkylcarbamoyl.

In one embodiment, R₄ is hydrogen, optionally substituted C₁₋₆ alkyl,optionally substituted C₁₋₆ alkylcarbonyl, optionally substituted C₆₋₁₀arylcarbonyl, or optionally substituted C₁₋₆ alkoxycarbonyl.

In one embodiment, R₄ is hydrogen, C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₆₋₁₀arylcarbonyl, C₁₋₆ alkoxycarbonyl, or C₁₋₆ alkylcarbamoyl.

In one embodiment, R₄ is hydrogen, C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₆₋₁₀arylcarbonyl, or C₁₋₆ alkoxycarbonyl.

In one embodiment, R₄ is hydrogen, C₁₋₄ alkyl, C₁₋₄ alkylcarbonyl, C₆arylcarbonyl, C₁₋₄ alkoxycarbonyl, or C₁₋₄ alkylcarbamoyl.

In one embodiment, R₄ is hydrogen, C₁₋₄ alkyl, C₁₋₄ alkylcarbonyl, C₆arylcarbonyl, or C₁₋₄ alkoxycarbonyl.

In one embodiment, R₄ is hydrogen or alkyl.

In one embodiment, R₄ is hydrogen or C₁₋₆ alkyl.

In one embodiment, R₄ is hydrogen, methyl, ethyl, acetyl, benzoyl,methoxycarbonyl, tert-butoxycarbonyl, or propylcarbamoyl.

In one embodiment, R₄ is hydrogen, methyl, ethyl, acetyl, benzoyl,methoxycarbonyl, or tert-butoxycarbonyl.

In one embodiment, R₄ is hydrogen or ethyl. In a preferred embodiment,R₄ is hydrogen.

A hydroxyl group, amino group, and/or carboxyl group in R₁, R₂, R₃,and/or R₄, when present, can be independently protected with aprotecting group. Such a compound is also within the scope of thepresent disclosure.

In some embodiments, the compound of the present disclosure can beexemplified as a compound represented by formula IB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof. R₁,R₂, and R₃ in formula IB are defined the same as those in formula IF.

In some embodiments, the compound of the present disclosure can beexemplified as a compound represented by formula IIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof. R₁,R₂, and R₃ in formula IIF are defined the same as those in formula IF.

In some embodiments, the compound of the present disclosure can beexemplified as a compound represented by formula IIB:

or an enantiomer thereof, or a salt thereof, or a solvate thereof. R₁,R₂, and R₃ in formula IIB are defined the same as those in formula IF.

The compound of the present disclosure is further described hereinafter.

While the compound of the present disclosure can have enantiomers andstereoisomers such as tautomers and geometric isomers depending on thetype of substituent, they are also encompassed by the presentdisclosure. Specifically, if there is one or more asymmetric carbonatoms in the compound of the present disclosure, there is a diastereomeror enantiomer, and a mixture of such a diastereomer and enantiomer, andisolated diastereomers and enantiomers are also encompassed by thecompound of the present disclosure.

The present disclosure is also intended to encompass various hydrates,solvates, and crystalline polymorphisms.

Furthermore, the compound of the present disclosure can be substitutedwith an isotope (e.g., ²H (or D), ³H (or T), ¹¹C, ¹³C, ¹⁴C, ¹³N, ¹⁵N,¹⁵O, ³⁵S, ¹⁸F, ¹²⁵I, or the like). These compounds are also encompassedby the compound of the present disclosure.

Furthermore, the scope of the present disclosure encompasses prodrugs ofthe compound of the present disclosure. In the present disclosure, aprodrug refers to a derivative that yields a compound represented byformula IF, IB, IIF, IIB, XXIF, XXIB, XXIIF, or XXIIB, or a relatedstructural formula by acid hydrolysis or enzymatic degradation in thebody. For example, if a compound represented by formula IF, IB, IIF,IIB, XXIF, XXIB, XXIIF, or XXIIB, or a related structural formulathereof has a functional group such as a hydroxyl group, amino group, orcarboxyl group or other substituents, these groups can be modified by aconventional method to manufacture a prodrug. Prodrug technologies aredescribed in, for example, C.G. Wermuth, “The Practice of MedicinalChemistry”, 4^(th)Ed., Academic Press, (2015), Chapter 28.

Examples for compounds having a carboxy group include compound whosecarboxyl group is modified to be an alkoxycarbonyl group,alkylthiocarbonyl group, or alkylaminocarbonyl group.

Examples of compounds having an amino group include compounds whoseamino group is substituted with an alkanoyl group to be an alkanoylaminogroup, compounds substituted with an alkoxycarbonyl group to be analkoxycarbonylamino group, compounds modified to have analkanoyloxymethylamino group, and compounds modified to havehydroxylamine.

Examples for compounds having a hydroxyl group include compounds whosehydroxyl group is substituted with an alkanoyl group to be analkanoyloxy group, phosphate ester, or alkanoyloxymethyloxy group.

Examples of the alkyl moiety of a group used for preparing a prodrugthereof include the alkyl group. The alkyl group is optionallysubstituted with, for example, an alkoxy group or the like. Preferredexamples thereof include the following.

For compounds whose carboxyl group is modified to be an alkoxycarbonylgroup, examples thereof include alkoxycarbonyl such as methoxycarbonyland ethoxycarbony, and alkoxycarbonyl substituted with an alkoxy groupsuch as methoxymethoxycarbonyl, ethoxymethoxycarbonyl,2-methoxyethoxycarbonyl, and 2-methoxyethoxymethoxycarbonyl, orprivaloyloxymethoxycarbonyl.

As used herein, “pharmaceutically acceptable salt” refers to an acidaddition salt or base addition salt which is pharmaceutically acceptablefor use. Specific examples of “pharmaceutically acceptable salts”include, but are not limited to, acid addition salts such as acetate,propionate, butyrate, formate, trifluoroacetate, maleate, fumarate,tartrate, citrate, stearate, succinate, ethylsuccinate, malonate,lactobionate, gluconate, glucoheptonate, benzoate, methanesulfonate,benzenesulfonate, para-toluenesulfonate (tosylate), laurylsulfate,malate, ascorbate, mandelate, saccharinate, xinafoate, pamoate,cinnamate, adipate, cysteine salt, N-acetyl cysteine salt,hydrochloride, hydrobromide, phosphate, sulfate, hydroiodide,nicotinate, oxalate, picrate, thiocyanate, undecanoate, acrylic acidpolymer salt, and carboxyvinyl polymer; inorganic base addition saltssuch as lithium salt, sodium salt, potassium salt, and calcium salt;organic base addition salts such as morpholine and piperidine; aminoacid addition salts such as aspartic acid and glutamic acid; and thelike.

In one embodiment, the compound of the present disclosure can beadministered directly, or as a formulation, medicament, or apharmaceutical composition using a suitable dosage form, by oral orparenteral administration. Specific examples of such dosage formsinclude, but are not limited to, tablets, capsules, powdered agents,granules, liquid agents, suspension, injection agents, patch-on agents,poultice, and the like. These formulations can be manufactured by aknown method using an additive that is commonly used as a pharmaceuticaladditive.

As these additives, an excipient, disintegrant, binding agent,fluidizer, lubricant, coating agent, solubilizing agent, solubilizingpromotor, thickener, dispersant, stabilizer, sweetener, flavoring agent,or the like can be used depending on the objective. Specific examples ofthese additives include, but are not limited to, lactose, mannitol,crystalline cellulose, low-substituted hydroxypropyl cellulose, cornstarch, partially pregelatinized starch, carmellose calcium,croscarmellose sodium, hydroxypropyl cellulose, hydroxypropylmethylcellulose, polyvinyl alcohol, magnesium stearate, sodium stearylfumarate, polyethylene glycol, propylene glycol, titanium oxide, talc,and the like.

The dosage of the compound of the present disclosure is appropriatelyselected depending on the subject targeted for administration, route ofadministration, disease, age of subject, body weight, and symptom. Forexample, the dosage is 0.01 mg as the lower limit (preferably 100 mg)and 10000 mg as the upper limit (preferably 6000 mg) per day for adultsfor oral administration. This amount can be administered once daily, ordivided into several doses.

In one embodiment, the compound of the present disclosure is a compoundwith an antiviral activity for a virus in the Lyssavirus genus. Thevirus in the Lyssavirus genus comprises a rabies virus, Lagos bat virus,mokola virus, Duvenhage virus, European bat 1 lyssavirus, European bat 2lyssavirus, Australian bat lyssavirus, and the like. The virus in theLyssavirus genus preferably comprises a rabies virus.

In one embodiment, the compound of the present disclosure is a compoundwith the ability to suppress or kill tumor or cancer. The tumor orcancer can be any tumor or cancer such as carcinoma, lymphoma, blastoma,sarcoma, or leukemia. Tumor and cancer can be squamous cell carcinoma,lung cancer such as small cell lung cancer, non-small cell lung cancer,or pulmonary adenocarcinoma, squamous cell carcinoma of the lung,peritoneal cancer, hepatoma, esophageal cancer, gastrointestinal cancer,pancreatic cancer, glioblastoma, uterine cancer such as cervical cancer,ovarian cancer, liver cancer, hepatocellular cancer, bladder cancer,hepatocellular carcinoma, breast cancer, colon cancer, colorectalcancer, epithelial or uterine carcinoma, salivary gland carcinoma,kidney cancer, liver cancer, prostate cancer, vulvar cancer, thyroidcancer, liver carcinoma, various types of head and neck cancer, bloodcancer (leukemia), prostate cancer, gastric cancer, fibrous cancer,glioma, melanoma, or the like.

The timing of dosing of the compound of the present disclosure andtherapeutic agents thereof is not limited. The compound and therapeuticagent can be administered concurrently or sequentially to a subjectbeing administered therewith. The compound of the present disclosure andtherapeutic agent thereof can be formulated as a combined agent. Thedosage of the therapeutic agent can be appropriately selected based onthe clinically used dose. The ratio of the compound of the presentdisclosure and therapeutic agent thereof can be appropriately selecteddepending on the subject of administration, route of administration,target disease, symptom, combination, or the like.

In one embodiment of the present disclosure, the compound of the presentdisclosure can be combined and administered concurrently or at differenttimes upon use of a pharmaceutical composition. Such a pharmaceuticalcomposition is also within the scope of the present disclosure.

Such a medicament, formulation, or pharmaceutical composition can bemanufactured by mixing the compound of the present disclosure and/or anaddition agent (e.g., anti-rabies gamma globulin formulation,antimicrobial agent, antiviral agent (e.g., ribavirin, amantadine, orthe like), sedative (e.g., ketamine, midazolam, or the like) or thelike) with any suitable component, together or separately, as a combinedagent, or as separate agents using any technology that is known in theart. An appropriate formulation such as a tablet, capsule, powder,granule, liquid agent, suspension, injection, patch, or poultice can beformulated by using any technology that is known in the art. If thecompound of the present disclosure and/or an addition agent (e.g.,anti-rabies gamma globulin formulation, antimicrobial agent, antiviralagent (e.g., ribavirin, amantadine, or the like), sedative (e.g.,ketamine, midazolam, or the like) or the like) are prepared as separateagents, they can be provided as a kit of two agents. The kit can provideone of the components as a single agent, with instructions (packageinsert or the like) instructing to combine and administer the othercomponent (for the compound of the present disclosure, the additionalagent; for the addition agent (e.g., anti-rabies gamma globulinformulation, antimicrobial agent, antiviral agent (e.g., ribavirin,amantadine, or the like), sedative (e.g., ketamine, midazolam, or thelike) or the like), the compound of the present disclosure) concurrentlyor at different times.

If the compound of the present disclosure is used as an activeingredient of a medicament, the compound is intended for use in not justhumans, but also other animals other than humans (cat, dog, cow, horse,bat, fox, mangoose, raccoon, and the like).

(Method of Manufacturing the Compound of the Present Disclosure)

Hereinafter, the method of manufacturing the compound of the presentdisclosure is described with examples, but the present disclosure is notlimited thereto.

The compound of the present disclosure can be manufactured by, forexample, the following manufacturing methods, but are not limited tosuch methods. These manufacturing methods can be appropriately improvedupon based on the expertise of those skilled in the art of organicsynthetic chemistry. Salts of the compounds used as a raw material canbe used in the following manufacturing method, as long as the reactionis not affected.

In the following manufacturing methods, even if use of a protectinggroup is not specifically described, a functional group other than thoseat the reaction point can be protected as needed and deprotected afterthe completion of a reaction or after a series of reations to obtain acompound of interest if one of the functional groups other than those atthe reaction point is altered under the reaction condition or if it isunsuitable for post-reaction processing. Common protecting groupsdescribed in the document (Peter G. M. Wuts, “Greene's Protective Groupsin Organic Synthesis”, 5^(th) Ed., John Wiley & Sons, Inc., Hoboken, NewJersey (2014)) or the like can be used as the protecting groups used inthese processes. A protecting group can be introduced or removed by amethod that is commonly used in organic synthetic chemistry (e.g.,method described in the aforementioned document or the like) or a methodin accordance thereto.

The starting material and intermediate in the following manufacturingmethods can be purchased as a commercially available product or areavailable by synthesis in accordance with a method described in a knowndocument or a known method from a known compound. Salts of the startingmaterial and intermediate can also be used, as long as the reaction isnot affected.

The intermediate and compound of interest in the following manufacturingmethods can also be converted into another compound encompassed by thepresent disclosure by appropriately converting their functional groups.A functional group can be converted in doing so by a method that iscommonly used in organic synthetic chemistry (e.g., method described inR. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., JohnWiley and Sons, Inc., New York (1999) or the like) or a method inaccordance therewith.

An inert solvent in the following manufacturing methods refers to asolvent that does not react with a raw material, reagent, base, acid,catalyst, ligand, or the like used in the reaction (hereinafter, alsoreferred to as “raw material or the like used in the reaction”). Asolvent used in each step can be used as an inert solvent even if thesolvent reacts with the raw material or the like used in the reaction,as long as the reaction of interest proceeds to result in a compound ofinterest.

The overview of compound synthesis related to the present disclosure isshown below. “B” and “F” following the Roman numerial compound numberindicate that a 5-membered ring comprising nitrogen is located in the“back” and “front”, respectively. In other words, a —C(═O)NH—R₂ groupattached to a 5-membered ring comprising nitrogen referred to as “back”,and a —C(═O)NH—R₂ that is not attached to a 5-membered ring comprisingnitrogen is referred to as “front”.

Synthesis Scheme 1

Synthesis of Compound III

Compound III can be manufactured by, for example, the followingmanufacturing method.

(1) Route 1-1 Synthesis from Compound VII and Compound VIII

(2) Route 1-2 Synthesis from Compound VII and Compound VIII throughProtection of Amine

(3) Route 1-3 Synthesis from Compound XI and Compound XII

wherein X_(L) represents a leaving group in a nucleophilic substitutionreaction. Examples thereof include halogen (e.g., chlorine, bromine, oriodine), sulfate esters (—OSO₃H and the like), and sulfonyl-O— groups(e.g., methanesulfonyl-O—, toluenesulfonyl-O—, and the like).(4) Route 1-4 Synthesis from Compound XI and Compound XIII

(5) Route 1-5 Synthesis from Compound VII and Compound XIV

wherein if R₁ in compound III can be expressed as —CH₂—R₁′, R₁ incompound III can be replaced with —CH₂—R₁′ to express compound III ascompound III′.

In the formula, R₁ is as defined in item 1 or Al herein, and “Protect”is a protecting group of amino group. Examples of protecting groups ofan amino group include an ethoxycarbonyl group, tert-butoxycarbonylgroup, acetyl group, benzoyl group, trifluoroacetyl group,benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group,triphenylmethyl group, methanesulfonyl group, p-toluenesulfonyl group,trimethylsilyl group, benzyloxycarbonyl group, 3- or4-chlorobenzyloxycarbonyl group, benzyl sulfonyl group, benzyl group,4-nitrobenzyl group, 4-methoxybenzyl group, methyl group, ethyl group,and the like.

A compound that is commercially available or a compound manufactured bya known method can be used as a starting raw material compound.

Synthesis Scheme 2

Synthesis of compound V

A compound of formula V can be manufactured by, for example, thefollowing manufacturing method.

(1) Route 2-1 Synthesis from Compound XVI and Compound XVII

wherein R₈ indicates alkoxy, aryloxy, hydroxy, or halogen. Examplesthereof include an ethoxy group. This systhesis is achieved by variousreactions known to those skilled in the art. If R₂ is aryl, compound Vcan be synthesized in accordance with the method described in C. W.Cheung, M. L. Ploeger, and X. Hu, Nature Communications 2017, 8, 14878.(2) Route 2-2 Synthesis from Compound XVIII

wherein R₂ is as defined in item 1 or Al herein. A compound that iscommercially available or a compound that is manufactured by a knownmethod can be used as the starting compound.

Synthesis Scheme 3

Synthesis of Compound VI

A compound of formula VI can be manufactured from compound III andcompound IV by, for example, the following manufacturing method.

wherein R₁ and R₃ are as defined in item 1 or Al herein.

Synthesis Scheme 4

Compound of Formula IIF and Compound of Formula IIB-Route 1

A compound of formula IIF and compound of formula IIB can bemanufactured, for example, from three components through one-potsynthesis in accordance with a known method (e.g., method described inBioorg. Med. Chem. 23 (2015) 2629-2635, Tetrahedron 63 (2007) 6004-6014,Eur. J. Org. Chem. 2009, 2185-2189, Eur. J. Org. Chem. 2011, 2354-2359or the like).

wherein R₁, R₂, and R₃ are as defined in item 1 or Al herein.

Synthesis Scheme 5

Compound of Formula IIF and Compound of Formula IIB-Route 2

A compound of formula IIF and compound of formula IIB can bemanufactured, for example, from two components as described below.

wherein R₁, R₂, and R₃ are as defined in item 1 or Al herein.

Synthesis Scheme 6

Synthesis of Compound IF and Compound IB

Step 6-1

Reduction of Imine

Compound IF (i.e., compound of formula IF) or compound IB (i.e.,compound of formula IB) can be manufactured, for example, from compoundIIF (i.e., compound of formula BF) or compound IIB (i.e., compound offormula IIB) by reduction as described below. However, R₄ therein is H.

Step 6-2

Modification of Amine of Piperidine ring

Amine of a piperidine ring of compound IF or compound IB can bemodified, for example by alkylation, amidation, or the like as follows.

Synthesis Scheme 7

Synthesis of Compound V′

A compound of formula V′ can be manufactured by, for example, thefollowing manufacturing method.

(1) Route 7-1 Synthesis from Compound XVI and Compound XVII′

A compound of formula V′ can be manufactured under the same condition asRoute 2-1 of Synthesis Scheme 2. R₈ indicates alkoxy, aryloxy, hydroxy,or halogen.

(2) Route 7-2 Synthesis from Compound XVIII′

wherein R_(2A) and R_(2B) are as defined in item 1 herein. A compoundthat is commercially available or a compound manufactured by a knownmethod can be used as a starting raw material compound.

Synthesis Scheme 8

Synthesis of Compound of Formula XXIIF and Compound of FormulaXXIIB-Route 1

A compound of formula XXIIF and a compound of formula XXIIB can besynthesized under the same condition as Synthesis Scheme 4.

wherein R₁, R_(2A), R_(2B), and R₃ are as defined in item 1 herein.

Synthesis Scheme 9

Synthesis of Compound of Formula XXIIF and Compound of FormulaXXIIB-Route 2

A compound of formula XXIIF and compound of formula XXIIB can bemanufactured, for example, from two components as described below.

wherein R₁, R_(2A), R_(2B), and R₃ are as defined in item 1 herein.

Synthesis Scheme 10

Synthesis of Compound XXIF and Compound XXIB

Step 10-1

Reductin of Imine

Under the same condition as step 6-1 of Synthesis Scheme 6, compoundXXIF (i.e., compound of formula XXIF) or compound XXIB (i.e., compoundof formula XXIB) can be manufactured, for example, from compound XXIIF(i.e., compound of formula XXIIF) or compound XXIIB (i.e., compound offormula XXIIB) by reduction as described below. However, R₄ therein isH.

Step 10-2

Modification of Amine of Piperidine Ring

Amine of a piperidine ring in compound XXIF or compound XXIB can bemodified by, for example, alkylation, amidation, or the like as follows.

R₄ in the product of this step is a group defined herein other than H.

The intermediate and compound of interest in the manufacturing methodsdescribed above can be isolated and purified by subjecting them to apurification method that is commonly used in organic synthesis chemistry(e.g., neutralization, filtration, extraction, washing, drying,concentration, recrystallization, various chromatography, or the like).Each intermediate can also be subjected to the subsequent reactionwithout any particular purification.

Optically active forms of the compound of the present disclosure can bemanufactured by using an optically active starting material orintermediate, or by optically resolving a racemate of the final productor intermediate. Examples of optional resolution methods include, butare not limited to, separation method using an optically active columnor a separation method such as fractional crystallization method. Adiastereomer of the compound of the present disclosure can bemanufactured by, for example, but not limited to, a separation methodsuch as column chromatography or fractional crystallization.

A pharmaceutically acceptable salt of a compound represented by formulaIF, IB, IIF, IIB, XXIF, XXIB, XXIIF, or XXIIB, or a related structuralformula can be manufactured by, for example, but not limited to, mixinga compound represented by formula IF, IB, IIF, IIB, XXIF, XXIB, XXIIF,or XXIIB, or a related structural formula with a pharmaceuticallyacceptable acid or base in a solvent such as water, methanol, ethanol,2-prpanol, ethyl acetate, or acetone.

As used herein, “or” is used when “at least one or more” of the listedmatters in the sentence can be employed. When explicitly describedherein as “within the range of two values”, the range also includes thetwo values themselves.

Reference literatures such as scientific literatures, patents, andpatent applications cited herein are incorporated herein by reference tothe same extent that the entirety of each document is specificallydescribed.

The present disclosure has been described while showing preferredembodiments to facilitate understanding. While the present disclosure isdescribed hereinafter based on the Examples, the above descriptions andthe following Examples are provided for the sole purpose ofexemplification, not limitation of the present disclosure. Thus, thescope of the present disclosure is not limited to the embodiments andExamples that are specifically described herein and is limited only bythe scope of claims.

EXAMPLES

The present disclosure is specifically described based on the Examples.The scope of the present disclosure is not limited to the Examplesdescribed below.

For Thin Layer Chromatography (TLC), Merck's TLC Silica gel 60 F254 (25glass plate, 20×20 cm) and Fuji Silysia Chemical's CHROMATOREX NH-TLCPlates (20×20 cm) were used. As the developing solvent,chloroform-methanol mixed solvent system, ethyl acetate-methanol mixedsolvent system, or ethyl acetate-hexane mixed solvent system was used.Spots were checked using coloring with UV irradiation, ninhydrin,iodine, or phosphomolybdic acid (ethanol solution). An organic solventwas dried using anhydrous sodium sulfate and anhydrous magnesiumsulfate. For column chromatography, Fuji Silysia Chemical's cartridgecolumn CHROMATOREX Q-PACKS 130 (SIZE 10, 20, or 60) and DNH (SIZE 20) orShoko Science's Purif-Pack®-EX SI50 (SIZE 20 or 60) were used inaccordance with the amount of raw product to be purified. Silica gelthin layer chromatography for separation (PTLC: Preparative Thin LayerChromatography) used Merck's PLC Silica gel 60 F254 (20×20 cm;thickness: 0.5 mm; product number: 1.05744.0001; thickness: 1 mm;product number: 1.13895.0001) and Fuji Silysia Chemical's CHROMATOREXNH-PLCO5 (20×20 cm; thickness: 0.5 mm). Synthesized compounds wereidentified by LC/MS (Liquid Chromatography/Mass Spectrometry). Tables 1to 4 show the retention (tR) and m/z value [M+1]⁺. For measurement,Shimadzu's LCMS-2020 system was used, and Chemicals Evaluation andResearch Institute's L-column2 ODS, 3 μm, 3.0×50 mm was used as theanalysis column. The column oven was set to 40° C., and compounds weredetected by using both UV absorption (220 nm, 254 nm) and massspectrometry. Elution condition A or B shown below was used.

Elution Condition A:

Flow rate 1.5 mL/min, mobile phase a=aqueous 0.05% (v/v) trifluoroaceticacid solution, mobile phase b=0.05% (v/v) trifluoroacetic acidcontaining acetonitrile; 0-0.9 minutes, linear gradient, A:B (95:5)-A:B(10:90), 0.9-2 minutes

Elution Condition B:

Flow rate 1.0 mL/min, mobile phase a=aqueous 0.05% (v/v) formic acidsolution, mobile phase b=0.05% (v/v) formic acid containing acetonitril;0-0.9 minutes, linear gradient, A:B (95:5)-A:B (10:90), 0.9-2 minutes

Elution Condition B1:

Flow rate 1.0 mL/min, mobile phase a=aqueous 0.05% (v/v) formic acidsolution, mobile phase b=0.05% (v/v) formic acid containingacetonitrile; 0.1-2.0 minutes, linear gradient, A:B (95:5)-A:B (60:40),2.0-3.0 minutes, linear gradient, A:B (60:40)-A:B (10:90), 3.0-4.0minutes

Furthermore, LC/MS measurement used the following instrument andmeasurement conditions.

Measurement Condition C:

Shimadzu's LCMS-2020 system was used, and Chemicals Evaluation andResearch Institute's L-column2 ODS, 3 μm, 3.0×50 mm was used as theanalysis column. The column oven was set to 40° C., and the compound wasdetected by using both UV absorption (220 nm, 254 nm) and massspectrometry.

Elution condition: flow rate of 1.5 mL/min, mobile phase a=aqueous 0.05%(v/v) trifluoroacetic acid solution, mobile phase b=0.05% (v/v)trifluoroacetic acid containing acetonitrile

TABLE A1 Time (min) Ratio of mobile phase b (%) 0.0  5 0.01-0..89 5-90linear gradient 0.9 90  2.00 90

Measurement Condition D:

The same apparatus as measurement condition C was used.

Elution condition: flow rate of 1.5 mL/min, mobile phase a=aqueous 0.05%(v/v) trifluoroacetic acid solution, mobile phase b=0.05% (v/v)trifluoroacetic acid containing acetonitrile

TABLE A2 Time (min) Ratio of mobile phase b (%) 0.0 0 0.5 0 0.51-1.390-70 linear gradient 1.4 70 1.5 90  2.00 90

Measurement Condition E:

The same apparatus as measurement condition C was used.

Elution condition: flow rate of 1.5 mL/min, mobile phase a=5 mM NH₄HCO₃containing water/acetonitrile=900/100 (v/v), mobile phase b=5 mM NH₄HCO₃containing water/acetonitrile=100/900 (v/v)

TABLE A3 Time (min) Ratio of mobile phase b (%) 0.0 0 0.5 0 0.51-1.390-70 linear gradient 1.4 70 1.5 90  2.00 90

Measurement Condition F:

Waters' Alliance 2695 Separation Module system was used, and YMC'sYMC-Triart C18, 5 μm, 3.0×50 mm was used as the analysis column. Thecolumn oven was set to 30° C., and the compound was detected using bothUV absorption (220 nm) and mass spectrometry.

Elution condition: flow rate of 1.27 mL/min, mobile phase a=aqueous0.05% (v/v) trifluoroacetic acid solution, mobile phase b=0.05% (v/v)trifluoroacetic acid containing acetonitrile

TABLE A4 Time (min) Ratio of mobile phase b (%) 0.0 10 1.0 10 1.0-1.510-30 gradient 1.5-4.5 30-70 gradient 4.5-5.0 70-90 gradient 6.0 90

Measurement Condition G:

The same apparatus as measurement condition F was used.

Elution condition: flow rate of 1.27 mL/min, mobile phase a=aqueous0.05% (v/v) trifluoroacetic acid solution, mobile phase b=0.05% (v/v)trifluoroacetic acid containing acetonitrile

TABLE A5 Time (min) Ratio of mobile phase b (%) 0.0 1 1.0 1 1.0-4.0 1-40 gradient 4.0-5.0 40-90 gradient 6.0 90 

Measurement Condition H:

Waters' 2767 system was used, and YMC's YMC-Triart C18, 5 μm, 4.6×50 mmwas used as the analysis column. The column oven was set to 25° C., andcompound was detected using UV absorption (220 nm), mass spectrometry,and ELS (Evaporative Light Scattering).

Elution condition: flow rate of 2 mL/min, mobile phase a=aqueous 0.1%(v/v) trifluoroacetic acid solution, mobile phase b=0.1% (v/v)trifluoroacetic acid containing acetonitrile

TABLE A6 Time (min) Ratio of mobile phase b (%) 0.0 5 0.5 5 0.5-3.0 5-95gradient 5.0 95 

Measurement Condition I:

Waters' H-class/SQD2 system was used, and Waters' ACQUITY UPLC BEH C181.7 μm, 2.1×50 mm was used as the analysis column. A compound wasdetected using both UV absorption (220 nm) and mass spectrometry.

Elution condition: flow rate of 0.6 mL/min, mobile phase a=aqueous 0.1%(v/v) formic acid solution, mobile phase b=0.1% (v/v) formic acidcontaining acetonitrile

TABLE A7 Time (min) Ratio of mobile phase b (%) 0.0 2 2.0-2.6 2-1002.6-3.0 100 

Measurement Condition J:

The same apparatus as measurement condition F was used.

Elution condition: flow rate of 1.27 mL/min, mobile phase a=aqueous0.05% (v/v) trifluoroacetic acid solution, mobile phase b=0.05% (v/v)trifluoroacetic acid containing acetonitrile

TABLE A8 Time (min) Ratio of mobile phase b (%) 0.0 10 1.0 10 1.0-2.010-60 gradient 2.0-5.0 60-99 gradient 5.0-6.0 99

Nuclear Magnetic Resonance (NMR) was measured using Bruker AVANCE III400 MHz Spectrometer (resonant frequency: ¹H: 400 MHz, ¹³C: 100 MHz) andBruker AVANCE III 300 MHz Spectrometer (resonant frequency: ¹H: 300 MHz,¹³C: 75 MHz). For the measurement of X-ray crystal structure, RigakuCorporation's single crystal X-ray diffractometer XtaLAB P200 was used.Cu-Ka rays monochromed with a multilayer mirror were used as the source.The structure was determined by a direct method using SIR2008. Thestructure was refined by the full-matrix least-squares method withrespect to F2 using SHELEX-2014/7. Non-hydrogen atoms were refined withanisotropic atomic displacement parameters.

The abbreviations described above and the following abbreviations arealso used in the Examples to simplify the description.

-   s: singlet-   d: doublet-   t: triplet-   m: multiplet-   dd: double doublet-   J: coupling constant-   Hz: Hertz-   δ: chemical shift-   min: minute-   RT and tR: retention-   CDCl₃: deuterated chloroform-   Me: methyl-   Et: ethyl-   Pr: propyl-   i-Pr: isopropyl-   i-Bu: isobutyl-   s-Bu and sec-Bu: secondary butyl-   ^(t)Bu, tBu and tert-Bu: tertiary butyl-   i-Pnt: isopentyl-   Hxy: n-hexyl-   Ac: acetyl-   Bz: benzoyl-   Bnzl: benzyl-   3-Me-Bnzl: 3-methylbenzyl-   4-Me-Bnzl: 4-methylbenzyl-   3-MeO-Bnzl: 3-methoxybenzyl-   4-MeO-Bnzl: 4-methoxybenzyl-   4-OH-Bnzl: 4-hydroxybenzyl-   3-F-Bnzl: 3-fluorobenzyl-   4-F-Bnzl: 4-fluorobenzyl-   3-Cl-Bnzl: 3-chlorobenzyl-   4-Cl-Bnzl: 4-chlorobenzyl-   3,4-Cl₂-Bnzl: 3,4-dichlorobenzyl-   4-tBuO-Bnzl: 4-(tert-butoxy)benzyl-   4-Nt-Bnzl: 4-nitrobenzyl-   Cbx-E and 2-Cbx-Et: 2-carboxyethyl-   Cbm-M: 2-amino-2-oxoethyl or carbamoylmethyl-   Cbm-E: 3-amino-3-oxopropyl or 2-carbamoylethyl-   tBOC-E: 2-(tert-butoxycarbonyl)ethyl or 3-(tert-butoxy)-3-oxopropyl-   Gun-Pr and 3-Gun-Pr: 3-guanidinopropyl-   Hdr-M: hydroxymethyl-   Hdr-E and 2-OH-Et: 2-hydroxyethyl-   tBuO-E and 2-OtBu-Et: 2-(tert-butoxy)ethyl-   Ph-Et: 2-phenylethyl-   Ph-Pr: 3-phenylpropyl-   Ph-Bu: 4-phenylbutyl-   Np-M and 1-Npm: naphthalen-l-ylmethyl-   2-Npm: naphthalen-2-ylmethyl-   Np-E: 2-(naphthalen-l-yl)ethyl-   Cpm: cyclopentylmethyl-   Chm: cyclohexylmethyl-   Boc and tBOC and ^(t)BOC: tert-butoxycarbonyl-   TBSO-E and 2-OTBS-Et: 2-(tert-butyldimethylsilyloxy)ethyl

Example 1 Synthesis of Compound Synthesis Example for Compound VSynthesis of N-benzyl-1,2,4-triazine-3-carboxamide

Ethyl 1,2,4-triazine-3-carboxylate (1.53 g,10.0 mmol) was dissolved inmethanol (10.0 mL), and phenylmethaneamine (1.18 g, 11.0 mmol) wasadded. The mixture was then stirred for 3 hours at 50° C. Methanol wasevaporated under reduced pressure, and the resulting residue waspurified by column chromatography (column: Purif-Pack Si50, Size 60,eluent: ethyl acetate-methanol (gradient from 0% to 15%)). A fraction ofa compound of interest was concentrated. The eluted crystal was filteredout to obtain the aforementioned compound (1.25 g, yield: 58%).

Under the same conditions as this reaction, the following compounds weresynthesized.

-   N-(naphthalen-1-ylmethyl)-1,2,4-triazine-3-carboxamide-   tert-butyl (4-(1,2,4-triazine-3-carboxamide)butyl)carbamate-   N-(4-(tert-butoxy)benzyl)-1,2,4-triazine-3-carboxamide-   N-isobutyl-1,2,4-triazine-3-carboxamide-   N-(4-methylbenzyl)-1,2,4-triazine-3-carboxamide-   N-phenethyl-1,2,4-triazine-3-carboxamide-   N-(3-methylbenzyl)-1,2,4-triazine-3-carboxamide-   N-(3-chlorobenzyl)-1,2,4-triazine-3-carboxamide-   N-(4-chlorobenzyl)-1,2,4-triazine-3-carboxamide-   N-(2-(naphthalen-l-yl)ethyl)-1,2,4-triazine-3-carboxamide-   tert-butyl    3-(2-(1,2,4-triazine-3-carboxamide)ethyl)-1H-indol-1-carboxylate-   N-(3,4-dichlorobenzyl)-1,2,4-triazine-3-carboxamide

Synthesis Example for Compound V Synthesis ofN-(2-hydroxyethyl)-1,2,4-triazine-3-carboxamide

Ethyl 1,2,4-triazine-3-carboxylate (76.5 mg,0.500 mmol) was dissolved inethanol (1.00 mL), and 2-aminoethanol (24.2 mg, 0.525 mmol) was added.The mixture was then stirred for 3 hours at room temperature. Methanolwas evaporated under reduced pressure, and the resulting residue waspurified by column chromatography (column: Purif-Pack Si50, Size 20,eluent: ethyl acetate-methanol (gradient from 0% to 30%)). A fraction ofa compound of interest was concentrated to obtain the aforementionedcompound (44.8 mg, yield: 53%).

Under the same conditions as this reaction, the following compound wassynthesized.

-   N-(cyclohexylmethyl)-1,2,4-triazine-3-carboxamide

Synthesis Example for Compound V Synthesis of tert-butyl3-(1,2,4-triazine-3-carboxamide)propanoate

Triethylamine (0.245 mL, 1.75 mmol) was added to an ethanol (2.00 mL)solution of tert-butyl 3-aminopropanoate⋅HCl (272 mg, 1.50 mmol). Amethanol (1.00 mL) suspension of ethyl 1,2,4-triazine-3-carboxylate(76.0 mg, 0.500 mmol) was added thereto. The mixture was stirred for 4hours at room temperature. Ethanol was evaporated under reducedpressure. The residue was dissolved in ethyl acetate. The organic layerwas washed with 10% citric acid water and 5% bicarbonate aqueoussolution and dried with anhydrous sodium sulfate. The solvent wasevaporated. The resulting residue was purified by column chromatography(column: Purif-Pack Si50, Size 20, eluent: hexane-ethyl acetate(gradient from 60% to 100%)) to obtain the aforementioned compound (65.7mg, yield: 52%).

Synthesis Example for Compound XV Synthesis of 4-methylpentanal

A methylene chloride (40.0 mL) solution of acetic acid (0.0994 mL, 1.30mmol) and 4-methylpentan-1-ol (1.49 mL, 11.8 mmol) was slowly addeddropwise into a methylene chloride (45.0 mL) solution of1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martinperiodinane) (5.25 g, 12.4 mmol) at room temperature. After completionof the addition, the mixture was stirred for another hour, and thendiethyl ether (280 mL) was added. An aqueous 1.30M sodium hydroxidesolution (200 mL) was added to the organic layer and stirred for 10minutes at room temperature. The organic layer was washed with anaqueous 1.30M sodium hydroxide solution (90.0 mL) and (50.0 mL). Afterdrying with anhydrous sodim magnesium sulfate, the solvent was carefullyevaporated to obtain the aforementioned compound (1.01 g, 86%).

Under the same conditions as this reaction, the following compound wassynthesized.

-   5-methylhexanal

Synthesis Example for Compound III Synthesis ofN-benzylprop-2-en-1-amine

(Bromomethyl)benzene (0.992 mL, 8.35 mmol) was gradually added dropwiseto a suspension of anhydrous potassium carbonate (1.39 g, 10.0 mmol) andprop-2-en-1-amine (7.53 mL, 100 mmol) and then stirred for 3 hours atroom temperature. The solids were filtered and washed with methylenechloride. The combined organic layer was evaporated under reducedpressure. The resulting residue was purified with CHROMATOREX Q-PACKSI30 SIZE 20 (hexane: ethyl acetate=50%:50% to 0%:100%) to obtain theaforementioned compound (934 mg, yield: 76%).

Under the same conditions as this reaction, the following compound wassynthesized.

-   N-(3,4-dichlorobenzyl)prop-2-en-1-amine

Synthesis Example for Compound III Synthesis ofN-(cyclohexylmethyl)prop-2-en-1-amine

Prop-2-en-1-amine (3.42 g, 60.0 mmol) was added dropwise to a methanol(40.0 mL) solution of cyclohexanecarbaldehyde (7.06 g, 63.0 mmol) whilecooling with ice. After the completion of the addition, sodiumtetrahydroborate (0.850 g, 22.0 mmol) was resolved and added whilecooling with ice, and the mixture was stirred for another hour. Methanolwas evaporated under reduced pressure. Ethyl ether was added to theresidue. The organic layer was washed with saturated saline and driedwith anhydrous sodium sulfate and then concentrated under reducepressure. The residue was evaporated under reduced pressure to obtainthe aforementioned compound (7.35 g, 80%, boiling point, 79 to 84°C./9.1 mmHg).

Under the same conditions as this reaction, the following compounds weresynthesized.

-   N-isobutylprop-2-en-1-amine-   N-allyl-3-methylbutan-1-amine

Synthesis Example for Compound III Synthesis ofN-(4-tert-butoxybenzyl)prop-2-en-1-amine

A methanol (2.00 mL) solution of 4-tert-butoxybenzaldehyde (468 mg, 2.63mmol) was added dropwise to a methanol (3.00 mL) solution ofprop-2-en-1-amine (143 mg, 2.50 mmol) while cooling with ice. After thecompletion of the addition, sodium tetrahydroborate (35.0 mg, 0.920mmol) was resolved and added while cooling with ice, and the mixture wasstirred for another hour. Methanol was evaporated under reducedpressure. Ethyl acetate was added to the residue. The organic layer waswashed with saturated saline and dried with anhydrous sodium sulfate andthen concentrated under reduce pressure. The resulting residue waspurified by column chromatography (column: Purif-Pack Si50, Size 60,eluent: hexane-ethyl acetate (gradient from 20% to 100%) and then ethylacetate-methanol (gradient from 0% to 15%)) to obtain the aforementionedcompound (370 mg, yield: 68%).

Under the same conditions as this reaction, the following compounds weresynthesized.

-   N-(naphthalen-1-ylmethyl)prop-2-en-1-amine-   N-(3,4-dichlorobenzyl)prop-2-en-1-amine

Synthesis Example: IIB-1 and IIF-1 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IIB-1) and(3S*,3aR*,6S*,7R*,7aR*)-N,7-dibenzyl-1-isobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IIF-1)

4 A molecular sieves (850 mg), 3-phenylpropanal (0.157 mL, 1.19 mmol),and N-isobutylprop-2-en-1-amine (purity: 90%, 150 mg, 1.19 mmol) wereadded to a chloroform (8.50 mL) solution ofN-benzyl-1,2,4-triazine-3-carboxamide (III) (170 mg, 0.794 mmol), andheated and refluxed for 10 hours. The molecular sieves were filtered andwashed twice with chloroform (5.00 mL). The combined organic layer wasevaporated under reduced pressure. The resulting residue was purifiedwith CHROMATOREX Q-PACK SI30 SIZE 60 (ethyl acetate:methanol=100%:0% to96%:4%) to obtain the aforementioned compounds (IIF-1) (86.9 mg, yield:26%, RT=1.14 minutes (B method), [M+1]⁺=416) and (IIB-1) (149 mg, yield:45%, RT=1.19 minutes (B method),[M+1]⁺=416).

Synthesis Example: IIB-29 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N-(4-aminobutyl)-7-benzyl-1-isobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(JIB-29)

Formic acid (300 μL) was added to(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(4-((tert-butoxycarbonyl)amino)butyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IIB-30) (9.30 mg, 0.0187 mmol) and incubated overnight at roomtemperature. Formic acid was evaporated under reduced pressure to obtaina diformic acid salt of the aforementioned compound (7.70 mg, yield:84%, RT=0.71 minutes (A method), [M+1]⁺=397).

Synthesis Example: IIF-26 Synthesis of3-((3S*,3aR*,6S*,7R*,7aR*)-7-benzyl-1-isobutyl-1,2,3,3a,7,7a-hexahydro-1H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide)propanoicacid (II-26)

Formic acid (1.00 mL) was added to(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl-1-isobutyl-N-(2-(tert-butoxy)-2-oxoethyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IIF-27) (30.4 mg, 0.0660 mmol), and heated overnight at 50° C. Formicacid was evaporated under reduced pressure to obtain a monoformic acidsalt of the aforementioned compound (29.7 mg, yield: 100%, RT=0.75minutes (A method), [M+1]⁺=398).

Synthesis Example: IIB-28 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N-(3-amino-3-oxopropyl)-7-benzyl-1-isobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(JIB-28)

3-((3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1-isobutyl-1,2,3,6,7,7a-hexahydro-1H-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide)propanoicacid (IIB-26) (15.0 mg, 0.0380 mmol) was dissolved in methanol (2.00mL), and ammonium water (25.0 μL) and4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (110mg, 0.397 mmol) were resolved and added 4 times each at roomtemperature. The solvent was evaporated under reduced pressure. Theresulting residue was purified by preparative PLC (Fuji SilysiaChemical's CHROMATOREX NH-PLCO5 (layer thickness 0.500 mm) (ethylacetate:methanol=9:1) to obtain the aforementioned compound (7.10 mg,yield: 47%, RT=0.79 minutes (A method), [M+1]⁺=397).

Tables 1 to 4 summarize the synthesized compounds of formula IIB andcompounds of IIF. The following abbreviations are used in the followingtables.

INT-iBu: N-isobutyl-1,2,4-triazine-3-carboxamide

INT-Bnzl: N-benzyl-1,2,4-triazine-3-carboxamide

SM1-iBu: N-isobutylprop-2-en-1-amine

SM1-Bnzl: N-benzylprop-2-en-1-amine

SM2-Ph: 3-phenylpropanal

SM2-Pnt: 4-methylpentanal

Since samples with a blank entry under Mass in the following tables areprepared based on Mass Number in HPLC, it can be understood that themolecular weight is inferred and confirmed based on the time ofretension (UV) of HPLC to identify the structure.

TABLE 1

Com- Raw Raw pound Synthesis material material number R₁ R₂ R₃ methodIntermediate 1 2 IIB-1 i-Bu Bnzl Bnzl EX INT-Bnzl SM1-iBu SM2-Ph IIB-2i-Bu i-Bu i-Bu IIB-1, INT-iBu SM1-iBu SM2-Pnt IIF-1 IIB-3 i-Bu i-Bu BnzlIIB-1, INT-iBu SM1-iBu SM2-Ph IIF-1 IIB-4 Bnzl i-Bu i-Bu IIB-1, INT-iBuSM1-Bnzl SM2-Pnt IIF-1 IIB-5 i-Bu Bnzl i-Bu IIB-1, INT-Bnzl SM1-iBuSM2-Pnt IIF-1 IIB-6 Bnzl i-Bu Bnzl IIB-1, INT-iBu SM1-Bnzl SM2-Ph IIF-1IIB-7 Bnzl Bnzl i-Bu IIB-1, INT-Bnzl SM1-Bnzl SM2-Pnt IIF-1 IIB-8 BnzlBnzl Bnzl IIB-1, INT-Bnzl SM1-Bnzl SM2-Ph IIF-1 IIB-9 i-Pnt Bnzl BnzlIIB-1, INT-Bnzl N-allyl- SM2-Ph IIF-1 3- methyl- butan- 1-amine IIB-Bnzl Bnzl i-Pnt IIB-1, INT-Bnzl SM1-Bnzl 5- 10 IIF-1 methyl- hexanalIIB- i-Bu Bnzl Ph-Et IIB-1, INT-Bnzl SM1-iBu 4- 11 IIF-1 phenyl- phenylbutanal IIB- i-Bu Ph-Et Bnzl IIB-1, N- SM1-iBu SM2-Ph 12 IIF-1phenethyl- 1,2,4- triazine-3- carboxamide IIB- i-Bu Bnzl 3-Me- IIB-1,INT-Bnzl SM1-iBu 3-(m- 13 Bnzl IIF-1 tolyl) propanal IIB- i-Bu Bnzl4-Me- IIB-1, INT-Bnzl SM1-iBu 3-(p- 14 Bnzl IIF-1 tolyl) propanal IIB-i-Bu 3-Me- Bnzl IIB-1, N-(3- SM1-iBu SM2-Ph 15 Bnzl IIF-1 methylbenzyl)-1,2,4- triazine-3- carboxamide IIB- i-Bu 4-Me- Bnzl IIB-1, N-(4- SM1-iBuSM2-Ph 16 Bnzl IIF-1 methylbenzyl)- 1,2,4- triazine-3- carboxamide IIB-i-Bu 3-Cl- Bnzl IIB-1, N-(3- SM1-iBu SM2-Ph 17 Bnzl IIF-1 chlorobenzyl)-1,2,4- triazine-3- carboxamide IIB- i-Bu 4-Cl- Bnzl IIB-1, N-(4- SM1-iBuSM2-Ph 18 Bnzl IIF-1 chlorobenzyl)- 1,2,4- triazine-3- carboxamide IIB-3,4- Bnzl i-Bu IIB-1, INT-Bnzl N-(3,4- SM2-Pnt 19 Cl₂- IIF-1 dichloroBnzl benzyl) prop-2- en-1- amine IIB- Bnzl 3,4-Cl₂- i-Bu IIB-1, N-(3,4-SM1-Bnzl SM2-Pnt 20 Bnzl IIF-1 dichloro- benzyl)-1,2,4- triazine-3-carboxamide IIB- Me Np-E Bnzl IIB-1, N-(2- N- SM2-Ph 21 IIF-1(naphthalen- methyl- -1- prop-2-en- yl)ethyl)- 1-amine 1,2,4-triazine-3- carboxamide IIB- i-Bu 4-(tert- Bnzl IIB-1, N-(4-tert-SM1-iBu SM2-Ph 23 butoxy) IIF-1 butoxybenzyl)- benzyl 1,2,4- triazine-3-carboxamide IIB- i-Bu Np-M Bnzl IIB-1, N- SM1-iBu SM2-Ph 24 IIF-1((naphthalen- 1- yl)methyl)- 1,2,4- triazine-3- carboxamide IIB- i-BuHdr-E Bnzl IIB-1, N-(2- SM1-iBu SM2-Ph 25 IIF-1 hydroxyethyl)- 1,2,4-triazine-3- carboxamide IIB- i-Bu Cbx-E Bnzl IB-40 IIB-27 26 IIB- i-Bu2-(tert- Bnzl IIB-1, tert-butyl SM1-iBu SM2-Ph 27 butoxy)- IIF-13-(1,2,4- 2- triazine-3- oxoethyl carboxamide) propanoate IIB- i-BuCbm-E Bnzl EX IIB-26 28 IIB- i-Bu 4- Bnzl EX IIB-30 29 aminobutyl IIB-i-Bu 4- Bnzl IIB-1, tert-butyl SM1-iBu SM2-Ph 30 ((tert- IIF-1 4-(1,2,4-butoxy- triazine-3- carbonyl) carboxamide) amino) butyl- butyl carbamateIIB- i-Bu Chm Bnzl IIB-1, N- SM1-iBu SM2-Ph 31 IIF-1 (cyclohexyl-methyl)- 1,2,4- triazine-3- carboxamide IIB- i-Bu (tetra- Bnzl IIB-1, N-SM1-iBu SM2-Ph 32 hydro-2H- IIF-1 ((tetrahydro- pyran-2- 2H-pyran-yl)methyl 2- yl)methyl)- 1,2,4- triazine-3- carboxamide IIB- i-Bu Bnzl4- IIB-1, INT-Bnzl SM1-iBu tert- 34 ((tert- IIF-1 butyl butoxy 5-carbonyl) formyl amino) pentyl- butyl carbamate IIB- i-Bu Bnzl 3- IIB-1,INT-Bnzl SM1-iBu methyl 36 methoxy- IIF-1 4- 3- formyl oxo- butanoatepropyl IIB- i-Bu Bnzl Chm IIB-1, INT-Bnzl SM1-iBu 3- 38 IIF-1 cyclo-hexyl- propanal IIB- Chm Bnzl Bnzl IIB-1, INT-Bnzl N- SM2-Ph 39 IIF-1(cyclo- hexyl- methyl) prop- 2-en-1- amine IIB- 4-OH- Bnzl Bnzl IB-40IIB-41 40 Bnzl IIB- 4- Bnzl Bnzl IIB-1, INT-Bnzl N-(4- SM2-Ph 41 (tert-IIF-1 tert- butoxy) butoxy- benzyl benzyl)prop- 2-en- 1-amine IIB- Np-MBnzl Bnzl IIB-1, INT-Bnzl N- SM2-Ph 42 IIF-1 ((naphthalen- 1- yl)methyl)prop- 2-en-1- amine IIB- 3- Bnzl Bnzl IIB-1, INT-Bnzl N-(3- SM2-Ph 76(tert- IIF-1 (tert- butoxy)- butoxy)- 3- 3- oxopropyl oxopropyl)- prop-2-en-1- amine IIB- Bnzl Bnzl 4-OH- IIB-1, INT-Bnzl SM1-Bnzl 3-(4- 77Bnzl IIF-1 hydroxy- phenyl) propanal IIB- Me 2-(1- Bnzl IIB-1, N-(2-(1-N- SM2-Ph 78 (tert- IIF-1 (tert- methyl- butoxy- butoxy- prop-2-carbonyl)- carbonyl)-1H- en-1- 1H- indol-3- amine indol-3- yl)ethyl)-yl)ethyl 1,2,4- triazine-3- carboxamide IIB- Np-M Bnzl Pr IIB-1,INT-Bnzl N- pentanal 80 IIF-1 ((naphthalen- 1- yl)methyl) prop- 2-en-1-amine IIB- benzyl naphthalen- iso- IIB-1, 81 en-1- butyl IIF-1 ylmethylEX: described in the Examples LCMS Compound tR Mass Measurement numberR₁ R₂ R₃ (min) (M + H)⁺ conditon IIB-81 benzyl naphthalen- isobutyl 1.29467 B 1-ylmethyl IIB-82 benzyl 4-(trifluoro- isobutyl 1.29 484 B methyl)benzyl IIB-83 4-chlorobenzyl benzyl isobutyl 1.29 450 B IIB-843-chlorobenzyl benzyl isobutyl 1.30 450 B IIB-85 4-methoxybenzyl benzylisobutyl 1.23 446 B IIB-86 4-methylbenzyl benzyl isobutyl 1.27 430 BIIB-88 isobutyl isobutyl 4-chloro- 1.26 416 B benzyl IIB-89 isobutyl4-chloro- isobutyl 1.27 416 B benzyl IIB-90 isobutyl benzyl isopentyl1.26 396 B IIB-91 isopentyl benzyl isobutyl 1.26 396 B IIB-92 isobutylisopentyl benzyl 1.27 396 B IIB-93 4-hydroxy- benzyl isobutyl 1.19 432 Bbenzyl IIB-94 4-(dimethyl- benzyl isobutyl 1.27 459 B amino)benzylIIB-95 4-(tert-butyl) benzyl isobutyl 1.31 472 B benzyl IIB-964-(trifluoro- benzyl isobutyl 1.32 500 B methoxy)benzyl IIB-974-ethoxybenzyl benzyl isobutyl 1.25 460 B IIB-98 isopentyl isobutylbenzyl 1.26 396 B IIB-99 benzyl 4-hydroxy- isobutyl 1.17 432 B benzylIIB-100 4-methoxy- 4-hydroxy- isobutyl 1.17 462 B benzyl benzyl IIB-1014-hydroxy- benzyl isopentyl 1.20 446 B benzyl IIB-102 benzylnaphthalen-2- isobutyl 1.27 466 B ylmethyl IIB-103 isopentyl 4-chloro-isobutyl 1.28 431 B benzyl IIB-104 isopentyl 4-fluoro- isobutyl 1.26 414B benzyl IIB-105 benzyl pyridin-4-yl isobutyl 1.06 417 B methyl IIB-1064-methoxy- benzyl benzyl 0.99 480 C benzyl IIB-107 phenethyl benzyl2-(tert- 1.12 532 C butyldimethyl- silyloxy) ethyl IIB-108 cyclopentyl-4-hydroxy- 2-carboxy- 0.78 440 C methyl benzyl ethyl IIB-1094-nitrobenzyl 4-(tert-butoxy) 2-(tert- 1.03 605 C benzyl butoxy-carbonyl)ethyl IIB-110 i-Bu i-Pr Bnzl 3.09 368 F IIB-111 i-Bu i-Bu4-tBuO- 3.95 454 F Bnzl IIB-112 i-Bu Bnzl 4-tBuO- 4.05 488 F BnzlIIB-113 i-Bu tBOC-E 4-tBuO- 4.12 526 F Bnzl IIB-114 i-Bu s-Bu 4-tBuO-3.93 454 F Bnzl IIB-115 i-Bu 1-Npm 4-tBuO- 4.48 538 F Bnzl IIB-116 i-Bui-Pr 4-tBuO- 3.64 440 F Bnzl IIB-117 i-Bu 1-Npm tBOC-E 4.11 504 FIIB-118 i-Bu i-Pr tBOC-E 3.18 406 F IIB-119 i-Bu 1-Npm 1-Npm 4.39 516 FIIB-120 i-Bu i-Pr 1-Npm 3.52 418 F IIB-121 Bnzl 4-tBuO-Bnzl Bnzl 4.23522 F IIB-122 Bnzl i-Bu 4-tBuO- 4.11 488 F Bnzl IIB-123 Bnzl Bnzl4-tBuO- 4.20 522 F Bnzl IIB-124 Bnzl tBOC-E 4-tBuO- 4.27 560 F BnzlIIB-125 Bnzl Bnzl tBOC-E 3.72 488 F IIB-126 Bnzl 4-tBuO-Bnzl tBOC-E 4.22560 F IIB-127 Bnzl 1-Npm tBOC-E 4.18 538 F IIB-128 Bnzl i-Bu 1-Npm 3.98466 F IIB-129 Bnzl Bnzl 1-Npm 4.09 500 F IIB-130 Bnzl 4-tBuO-Bnzl 1-Npm4.55 572 F IIB-131 Bnzl tBOC-E 1-Npm 4.17 538 F IIB-132 Bnzl s-Bu 1-Npm3.96 466 F IIB-133 Bnzl 1-Npm 1-Npm 4.49 550 F IIB-134 Bnzl i-Pr 1-Npm3.71 452 F IIB-135 4-tBuO-Bnzl i-Bu Bnzl 3.92 488 F IIB-136 4-tBuO-BnzlBnzl Bnzl 4.57 522 F IIB-137 4-tBuO-Bnzl 1-Npm Bnzl 5.10 572 F IIB-1384-tBuO-Bnzl Bnzl tBOC-E 3.95 560 F IIB-139 4-tBuO-Bnzl 1-Npm tBOC-E 4.35610 F IIB-140 4-tBuO-Bnzl i-Bu 1-Npm 4.07 538 F IIB-141 4-tBuO-Bnzl Bnzl1-Npm 5.00 572 F IIB-142 4-tBuO-Bnzl tBOC-E 1-Npm 4.14 610 F IIB-1434-tBuO-Bnzl s-Bu 1-Npm 4.27 538 F IIB-144 4-tBuO-Bnzl 1-Npm 1-Npm 5.40622 F IIB-145 i-Bu 4-tBuO-Bnzl Bnzl 4.13 488 F IIB-146 i-Bu tBOC-E Bnzl3.66 454 F IIB-147 i-Bu s-Bu Bnzl 3.38 382 F IIB-148 i-Bu i-Bu tBOC-E3.44 420 F IIB-149 i-Bu Bnzl tBOC-E 3.63 454 F IIB-150 i-Bu 4-tBuO-BnzltBOC-E 4.18 526 F IIB-151 i-Bu s-Bu tBOC-E 3.46 420 F IIB-152 i-Bu i-Bu1-Npm 3.87 432 F IIB-153 i-Bu Bnzl 1-Npm 3.98 466 F IIB-154 i-Bu4-tBuO-Bnzl 1-Npm 4.44 538 F IIB-155 i-Bu tBOC-E 1-Npm 4.04 504 FIIB-156 Bnzl tBOC-E Bnzl 3.82 488 F IIB-157 Bnzl s-Bu Bnzl 3.55 416 FIIB-158 Bnzl 1-Npm Bnzl 4.21 500 F IIB-159 Bnzl i-Pr Bnzl 3.31 402 FIIB-160 Bnzl s-Bu 4-tBuO- 4.08 488 F Bnzl IIB-161 Bnzl 1-Npm 4-tBuO-4.61 572 F Bnzl IIB-162 Bnzl i-Pr 4-tBuO- 3.83 474 F Bnzl IIB-163 Bnzls-Bu tBOC-E 3.60 454 F IIB-164 Bnzl i-Pr tBOC-E 3.28 440 F IIB-1654-tBuO-Bnzl i-Pr Bnzl 3.70 474 F IIB-166 4-tBuO-Bnzl i-Pr tBOC-E 3.75512 F IIB-167 4-tBuO-Bnzl i-Pr 1-Npm 4.07 524 F IIB-168 tBOC-E i-Bu Bnzl3.77 454 F IIB-169 tBOC-E Bnzl Bnzl 3.86 488 F IIB-170 tBOC-E4-tBuO-Bnzl Bnzl 4.34 560 F IIB-171 tBOC-E s-Bu Bnzl 3.76 454 F IIB-172tBOC-E 1-Npm Bnzl 4.34 538 F IIB-173 tBOC-E i-Bu 4-tBuO- 4.30 526 F BnzlIIB-174 tBOC-E Bnzl 4-tBuO- 4.40 560 F Bnzl IIB-175 tBOC-E s-Bu 4-tBuO-4.31 526 F Bnzl IIB-176 tBOC-E 1-Npm 4-tBuO- 4.80 610 F Bnzl IIB-177tBOC-E i-Pr 4-tBuO- 4.05 512 F Bnzl IIB-178 tBOC-E i-Bu 1-Npm 4.13 504 FIIB-179 tBOC-E 4-tBuO-Bnzl 1-Npm 4.66 610 F IIB-180 tBOC-E s-Bu 1-Npm4.09 504 F IIB-181 tBOC-E 1-Npm 1-Npm 4.63 588 F IIB-182 1-Npm4-tBuO-Bnzl Bnzl 4.18 572 F IIB-183 1-Npm s-Bu Bnzl 3.82 466 F IIB-1841-Npm Bnzl 4-tBuO- 4.68 572 F Bnzl IIB-185 1-Npm tBOC-E 4-tBuO- 4.24 610F Bnzl IIB-186 1-Npm s-Bu 4-tBuO- 4.84 538 F Bnzl IIB-187 1-Npm 1-Npm4-tBuO- 4.85 622 F Bnzl IIB-188 1-Npm i-Pr 4-tBuO- 4.20 524 F BnzlIIB-189 1-Npm i-Bu tBOC-E 3.80 504 F IIB-190 1-Npm Bnzl tBOC-E 4.45 538F IIB-191 1-Npm 4-tBuO-Bnzl tBOC-E 4.84 610 F IIB-192 1-Npm s-Bu tBOC-E4.29 504 F IIB-193 1-Npm 1-Npm tBOC-E 4.49 588 F IIB-194 1-Npm Bnzl1-Npm 4.75 550 F IIB-195 1-Npm 4-tBuO-Bnzl 1-Npm 4.74 622 F IIB-1961-Npm tBOC-E 1-Npm 4.59 588 F IIB-197 1-Npm s-Bu 1-Npm 4.57 516 FIIB-198 i-Bu 4-tBuO-Bnzl i-Bu 4.04 454 F IIB-199 i-Bu tBOC-E i-Bu 3.35420 F IIB-200 i-Bu s-Bu i-Bu 3.25 348 F IIB-201 i-Bu 1-Npm i-Bu 4.00 432F IIB-202 i-Bu i-Pr i-Bu 2.97 334 F IIB-203 i-Bu (tBOC)Gun-Pr 4-tBuO-2.81 641 J Bnzl IIB-204 i-Bu 1-Npm (tBOC)Gun- 3.27 675 J Pr IIB-205 i-Bus-Bu 1-Npm 3.85 432 F IIB-206 Bnzl 4-tBuO-Bnzl i-Bu 4.13 488 F IIB-207Bnzl s-Bu i-Bu 3.45 382 F IIB-208 Bnzl i-Pr i-Bu 3.14 368 F IIB-209 Bnzli-Bu (tBOC)Gun- 3.22 625 J Pr IIB-210 Bnzl 4-tBuO-Bnzl (tBOC)Gun- 2.96675 J Pr IIB-211 tBOC-E i-Bu i-Bu 3.63 420 F IIB-212 tBOC-E Bnzl i-Bu3.83 454 F IIB-213 tBOC-E 4-tBuO-Bnzl i-Bu 4.35 526 F IIB-214 tBOC-Es-Bu i-Bu 3.68 420 F IIB-215 tBOC-E 1-Npm i-Bu 4.32 504 F IIB-216 tBOC-Ei-Pr i-Bu 3.41 406 F IIB-217 tBOC-E Bnzl 1-Npm 4.19 538 F IIB-218 tBOC-Ei-Pr 1-Npm 3.87 490 F IIB-219 1-Npm Bnzl i-Bu 3.62 466 F IIB-220 1-Npmi-Bu Bnzl 3.67 466 F IIB-221 1-Npm (tBOC)Gun-Pr Bnzl 3.97 709 F IIB-2221-Npm i-Bu 4-tBuO- 4.18 538 F Bnzl IIB-223 1-Npm i-Pr tBOC-E 3.62 490 FIIB-224 1-Npm 1-Npm (tBOC)Gun- 5.14 759 F Pr IIB-225 1-Npm i-Pr(tBOC)Gun- 3.15 661 F Pr IIB-226 1-Npm i-Bu 1-Npm 4.07 516 F IIB-2271-Npm (tBOC)Gun-Pr 1-Npm 2.99 459 F IIB-228 1-Npm i-Pr 1-Npm 3.90 502 FIIB-229 i-Bu (tBOC)Gun-Pr i-Bu 3.10 591 J IIB-230 i-Bu (tBOC)Gun-Pr Bnzl3.03 625 J IIB-231 i-Bu i-Bu (tBOC)Gun- 3.01 591 J Pr IIB-232 i-Bu Bnzl(tBOC)Gun- 3.02 625 J Pr IIB-233 i-Bu 4-tBuO-Bnzl (tBOC)Gun- 2.84 641 JPr IIB-234 i-Bu s-Bu (tBOC)Gun- 2.99 591 J Pr IIB-235 i-Bu i-Pr(tBOC)Gun- 2.90 577 J Pr IIB-236 i-Bu (tBOC)Gun-Pr 1-Npm 3.17 675 JIIB-237 Bnzl (tBOC)Gun-Pr i-Bu 3.19 625 J IIB-238 Bnzl (tBOC)Gun-Pr Bnzl3.26 659 J IIB-239 Bnzl (tBOC)Gun-Pr 4-tBuO- 2.84 675 J Bnzl IIB-240Bnzl i-Bu tBOC-E 3.56 454 F IIB-241 Bnzl Bnzl (tBOC)Gun- 3.28 659 J PrIIB-242 Bnzl s-Bu (tBOC)Gun- 3.04 625 J Pr IIB-243 Bnzl i-Pr (tBOC)Gun-2.99 611 J Pr IIB-244 Bnzl (tBOC)Gun-Pr 1-Npm 3.36 709 J IIB-245 tBOC-Ei-Pr Bnzl 3.45 440 F IIB-246 (tBOC)Gun-Pr 1-Npm i-Bu 3.65 657 J IIB-247(tBOC)Gun-Pr i-Pr i-Bu 3.21 577 J IIB-248 (tBOC)Gun-Pr 1-Npm Bnzl 3.75709 J IIB-249 (tBOC)Gun-Pr i-Pr Bnzl 3.24 611 J IIB-250 (tBOC)Gun-Pr1-Npm 4-tBuO- 3.30 725 J Bnzl IIB-251 (tBOC)Gun-Pr i-Pr 4-tBuO- 2.92 627J Bnzl IIB-252 (tBOC)Gun-Pr 1-Npm 1-Npm 3.86 759 J IIB-253 (tBOC)Gun-Pri-Pr 1-Npm 3.38 661 J IIB-254 1-Npm (tBOC)Gun-Pr i-Bu 4.29 675 F IIB-2551-Npm 1-Npm i-Bu 4.05 516 F IIB-256 1-Npm 1-Npm Bnzl 4.92 550 F IIB-257Bnzl tBOC-E i-Bu 3.73 454 F IIB-258 Bnzl 1-Npm (tBOC)Gun- 3.80 709 J PrIIB-259 4-tBuO-Bnzl i-Bu i-Bu 3.67 454 F IIB-260 4-tBuO-Bnzl Bnzl i-Bu3.67 488 F IIB-261 4-tBuO-Bnzl tBOC-E i-Bu 3.82 526 F IIB-2624-tBuO-Bnzl (tBOC)Gun-Pr i-Bu 3.38 641 F IIB-263 4-tBuO-Bnzl s-Bu i-Bu3.75 454 F IIB-264 4-tBuO-Bnzl 1-Npm i-Bu 4.22 538 F IIB-265 4-tBuO-Bnzli-Pr i-Bu 3.47 440 F IIB-266 4-tBuO-Bnzl tBOC-E Bnzl 3.88 560 F IIB-2674-tBuO-Bnzl (tBOC)Gun-Pr Bnzl 3.24 675 F IIB-268 4-tBuO-Bnzl s-Bu Bnzl3.85 488 F IIB-269 4-tBuO-Bnzl i-Bu tBOC-E 3.88 526 F IIB-2704-tBuO-Bnzl s-Bu tBOC-E 3.79 526 F IIB-271 4-tBuO-Bnzl i-Bu (tBOC)Gun-3.45 641 F Pr IIB-272 4-tBuO-Bnzl Bnzl (tBOC)Gun- 3.82 675 F Pr IIB-2734-tBuO-Bnzl s-Bu (tBOC)Gun- 3.38 641 F Pr IIB-274 4-tBuO-Bnzl 1-Npm(tBOC)Gun- 3.88 725 F Pr IIB-275 4-tBuO-Bnzl i-Pr (tBOC)Gun- 3.27 627 FPr IIB-276 4-tBuO-Bnzl (tBOC)Gun-Pr 1-Npm 3.74 725 F IIB-277(tBOC)Gun-Pr i-Bu i-Bu 4.52 591 F IIB-278 (tBOC)Gun-Pr Bnzl i-Bu 4.25625 F IIB-279 (tBOC)Gun-Pr 4-tBuO-Bnzl i-Bu 3.79 641 F IIB-280(tBOC)Gun-Pr s-Bu i-Bu 4.04 591 F IIB-281 (tBOC)Gun-Pr i-Bu Bnzl 4.39625 F IIB-282 (tBOC)Gun-Pr Bnzl Bnzl 4.30 659 F IIB-283 (tBOC)Gun-Pr4-tBuO-Bnzl Bnzl 3.82 675 F IIB-284 (tBOC)Gun-Pr s-Bu Bnzl 4.09 625 FIIB-285 (tBOC)Gun-Pr i-Bu 4-tBuO- 3.80 641 F Bnzl IIB-286 (tBOC)Gun-PrBnzl 1-Npm 4.57 709 F IIB-287 (tBOC)Gun-Pr s-Bu 1-Npm 4.49 675 F IIB-2881-Npm i-Bu i-Bu 3.65 432 F IIB-289 1-Npm 4-tBuO-Bnzl i-Bu 4.09 538 FIIB-290 1-Npm tBOC-E i-Bu 3.77 504 F IIB-291 1-Npm s-Bu i-Bu 3.71 432 FIIB-292 1-Npm i-Pr i-Bu 3.54 418 F IIB-293 1-Npm tBOC-E Bnzl 3.99 538 FIIB-294 1-Npm i-Pr Bnzl 3.69 452 F IIB-295 1-Npm (tBOC)Gun-Pr 4-tBuO-3.59 725 F Bnzl IIB-296 1-Npm i-Bu (tBOC)Gun- 4.00 675 F Pr IIB-2971-Npm Bnzl (tBOC)Gun- 4.17 709 F Pr IIB-298 1-Npm 4-tBuO-Bnzl (tBOC)Gun-3.65 725 F Pr IIB-299 Bnzl 1-Npm 3-Gun-Pr 2.70 509 F IIB-300 4-OH-Bnzl3-Gun-Pr i-Bu 2.47 441 F IIB-301 4-OH-Bnzl 1-Npm 3-Gun-Pr 2.90 525 FIIB-302 1-Npm 3-Gun-Pr 4-OH-Bnzl 2.70 525 F IIB-303 1-Npm i-Bu 3-Gun-Pr2.82 475 F IIB-304 1-Npm Bnzl 3-Gun-Pr 2.97 509 F IIB-305 1-Npm4-OH-Bnzl 3-Gun-Pr 2.77 525 F IIB-306 1-Npm s-Bu 3-Gun-Pr 2.82 475 FIIB-307 Bnzl Ph-Et i-Bu 0.97 430 C IIB-308 Ph-Et i-Bu Bnzl 1.00 430 CIIB-309 Chm i-Bu Bnzl 1.05 422 C IIB-310 Bnzl 4-F-Bnzl i-Bu 0.98 434 CIIB-311 Chm Bnzl i-Bu 1.04 422 C IIB-312 Bnzl Hxy i-Bu 1.08 410 CIIB-313 Ph-Et i-Bu i-Bu 0.99 396 C IIB-314 Ph-Et i-Bu 1-Npm 1.04 480 CIIB-315 Bnzl i-Bu Ph-Et 1.00 430 C IIB-316 4-F-Bnzl i-Bu Bnzl 1.00 434 CIIB-317 i-Bu 4-F-Bnzl Bnzl 0.99 434 C IIB-318 Ph-Et Bnzl i-Bu 0.98 430 CIIB-319 Bnzl i-Pnt i-Bu 1.00 396 C IIB-320 i-Bu Hxy Bnzl 1.05 410 CIIB-321 4-F-Bnzl Bnzl Bnzl 0.99 468 C IIB-322 Ph-Et Bnzl Bnzl 1.00 464 CIIB-323 Bnzl i-Bu i-Pnt 1.03 396 C IIB-324 4-F-Bnzl Bnzl i-Bu 0.98 434 C

Measure- Compound LCMS Mass ment number R₁ R_(2A) R_(2B) R₃ RT (min)(M + H)⁺ condition IIB- 2-Npm H Bnzl i-Bu 2.89 466 B1 325 IIB- i-Pnt H3- Bnzl 2.85 464 B1 326 Cl- Bnzl IIB- i-Pnt H 4- Bnzl 2.83 444 B1 327Me- Bnzl IIB- i-Pnt H 4- Bnzl 2.71 460 B1 328 MeO- Bnzl IIB- Me Hquinolin- Bnzl 2.09 439 B1 8- yl ethyl IIB- Me H quinolin- Bnzl 1.62 439B1 5- yl ethyl IIB- i-Bu H 4- Ph-Et 2.84 464 B1 331 Cl- Bnzl IIB- i-Bu H3- Ph-Et 2.68 464 B1 332 Cl- Bnzl IIB- i-Bu H 4- Ph-Et 2.70 460 B1 333MeO- Bnzl IIB- i-Bu H 4- Ph-Et 2.83 445 B1 334 Me- Bnzl IIB- i-Bu H 2-Ph-Et 2.92 480 B1 335 Npm IIB- i-Bu H Bnzl Ph-Pr 2.82 444 B1 336 IIB-i-Bu H 3- Ph-Pr 1.29 478 B 337 Cl- Bnzl IIB- i-Bu H 3-F- Ph-Pr 1.33 462B 338 Bnzl IIB- Cpm H 4- Cbx-E 1.10 440 B 339 OH- Bnzl IIB- i-Bu H 3-Ph-Pr 1.33 458 B 340 Me- Bnzl IIB- i-Bu H 3- Ph-Pr 1.29 474 B 341 MeO-Bnzl IIB- i-Bu H 3- Ph-Bu 1.33 492 B 342 Cl- Bnzl IIB- i-Bu H 3-F- Ph-Bu1.29 476 B 343 Bnzl IIB- i-Bu H 3- Ph-Bu 1.31 473 B 344 Me- Bnzl IIB-i-Bu H 3- Ph-Bu 1.36 488 B 345 MeO- Bnzl IIB- i-Bu H Bnzl Ph-Bu 1.29 458B 346 IIB- i-Pnt H 3-F- Ph-Pr 1.25 476 B 347 Bnzl IIB- 1-Npm H pent-Ph-Et 1.08 494 C 348 yl IIB- 1-Npm pyrrolidine ^(†) Ph-Et 0.96 478 C 349IIB- 1-Npm H cyclo- Ph-Et 1.07 506 C 350 hex- yl IIB- 1-Npm H cyclo-Ph-Et 1.05 492 C 351 pent- yl IIB- 1-Npm piperidine ^(†) Ph-Et 1.01 492C 352 IIB- 1-Npm H hept- Ph-Et 1.14 522 C 353 yl IIB- Hdr-E H 4- 1-Npm0.93 486 C 354 fluoro- phen- ethyl IIB- tBuO-E H 4- 1-Npm 1.07 542 C 355fluoro- phen- ethyl IIB- Pr H Chm Bnzl 1.00 408 C 356 IIB- 1-Npm H Hxy4- 1.13 522 C 357 methyl- phenethyl IIB- 1-Npm H Hxy 4- 1.18 550 C 358isopropyl phenethyl IIB- 1-Npm H Hxy 2- 1.15 558 C 359 (naphthalen- 2-yl)ethyl IIB- 1-Npm H Hxy cyclohexyl- 1.19 514 C 360 ethyl IIB- tBuO-E H4- 1-Npm 1.07 545 C 361 Cl- Bnzl IIB- tBuO-E H 4- 1-Npm 1.07 524 C 362Me- Bnzl IIB- Pr H Bnzl Chm 1.00 408 C 363 IIB- Pr H 2- Bnzl 0.95 416 C364 methyl- benzyl IIB- Pr H (1,2, Bnzl 1.01 456 C 365 3,4 tetra- hydro-naph- thalen- 1- yl) methyl IIB- Pr H Cpm Bnzl 0.96 394 C 366 IIB- Pr HBnzl Cpm 0.95 394 C 367 IIB- 1-Npm H Hxy 3- 1.13 522 C 368 methyl- phen-ethyl IIB- 4-Nt-Bnzl H Bnzl Bnzl 0.96 495 C 369 IIB- 4-Nt-Bnzl H HxyPh-Et 1.04 503 C 370 IIB- i-Pnt H 4-F- Bnzl 2.73 448 B1 371 Bnzl IIB-i-Pnt H Ph- Bnzl 2.76 444 B1 372 Et IIB- i-Pnt H 1- Bnzl 2.93 480 B1 373Npm IIB- i-Bu H 4-F- Ph-Et 2.73 448 B1 374 Bnzl IIB- i-Bu H Ph- Ph-Et2.76 444 B1 375 Et IIB- i-Bu H 1- Ph-Et 2.93 480 B1 376 Npm IIB-4-F-Bnzl H 1- Bnzl 2.98 518 B1 377 Npm IIB- 4-F-Bnzl H 1- i-Bu 1.30 484B 378 Npm IIB- tBuO-E H 4-F- 1-Npm 1.06 528 C 379 Bnzl IIB- tBOC-E HBnzl Ph-Et 1.02 502 C 380 IIB- 4-tBuO- H Bnzl Ph-Et 1.06 536 C 381 BnzlIIB- tBuO-E H Bnzl 1-Npm 1.05 510 C 382 IIB- Chm H tBuO- 1-Npm 1.07 516C 383 E IIB- 1-Npm H 4-F- TBSO-E 1.16 586 C 384 Bnzl IIB- i-Pnt H BnzlPh-Et 1.01 444 C 385 IIB- 1-Npm H 4-F- Hdr-E 0.91 472 C 386 Bnzl IIB-Hdr-E H 4-F- 1-Npm 0.91 472 C 387 Bnzl IIB- Cbx-E H Bnzl Ph-Et 0.88 446C 388 IIB- TBSO-E H Ph- 1-Npm 1.07 524 C 389 Et IIB- Ph-Et H Hxy 1-Npm1.08 508 C 390 IIB- Ph-Et H i-Bu 4-tBuO- 1.06 502 C 391 Bnzl IIB- Ph-EtH i-Bu 4-OH-Bnzl 0.89 446 C 392 IIB-393 Ph-Et H i-Bu TBSO-E 1.13 498 CIIB-394 Ph-Et H i-Bu Hdr-E 0.82 384 C IIB-395 Ph-Et H i-Bu i-Pnt 1.02410 C IIB-396 i-Bu H i-Bu 4-OH-Bnzl 0.85 398 C IIB-397 i-Bu H Bnzl4-OH-Bnzl 0.87 432 C IIB-398 i-Bu H 2- 4-OH-Bnzl 0.69 414 C Cbx- EtIIB-399 i-Bu H s-Bu 4-OH-Bnzl 0.85 398 C IIB-400 i-Bu H 1- 4-OH-Bnzl0.95 482 C Npm IIB-401 i-Bu H i-Pr 4-OH-Bnzl 0.80 384 C IIB-402 i-Bu H1- 2-Cbx-Et 0.89 448 C Npm IIB-403 i-Bu H i-Pr 2-Cbx-Et 0.72 350 CIIB-404 Bnzl H 4- Bnzl 0.90 466 C OH- Bnzl IIB-405 Bnzl H i-Bu 4-OH-Bnzl0.89 432 C IIB-406 Bnzl H 2- 4-OH-Bnzl 0.74 448 C Cbx- Et IIB-407 Bnzl HBnzl 2-Cbx-Et 0.82 432 C IIB-408 Bnzl H 4- 2-Cbx-Et 0.73 448 C OH- BnzlIIB-409 Bnzl H 1- 2-Cbx-Et 0.90 482 C Npm IIB-410 Bnzl H 4- 1-Npm 0.93,0.95 516 C * OH- Bnzl IIB-411 Bnzl H 2- 1-Npm 0.88 482 C Cbx- Et IIB-4124-OH-Bnzl H i-Bu Bnzl 0.89 432 C IIB-413 4-OH-Bnzl H 1- Bnzl 0.97 516 CNpm IIB-414 4-OH-Bnzl H Bnzl 2-Cbx-Et 0.76 448 C IIB-415 4-OH-Bnzl H 1-2-Cbx-Et 0.84 498 C Npm IIB-416 4-OH-Bnzl H i-Bu 1-Npm 0.93, 0.94 482C * IIB-417 4-OH-Bnzl H Bnzl 1-Npm 0.95 516 C IIB-418 4-OH-Bnzl H 2-1-Npm 0.82 498 C Cbx- Et IIB-419 4-OH-Bnzl H s-Bu 1-Npm 0.94 482 CIIB-420 4-OH-Bnzl H 1- 1-Npm 0.98, 1.00 566 C * Npm IIB-421 i-Bu H 4-Bnzl 0.88 432 C OH- Bnzl IIB-422 i-Bu H i-Bu 2-Cbx-Et 0.78 364 C IIB-423i-Bu H Bnzl 2-Cbx-Et 0.81 398 C IIB-424 i-Bu H 4- 2-Cbx-Et 0.71 414 COH- Bnzl IIB-425 i-Bu H s-Bu 2-Cbx-Et 0.77 364 C IIB-426 i-Bu H 4- 1-Npm0.94 482 C OH- Bnzl IIB-427 i-Bu H 2- 1-Npm 0.87 448 C Cbx- Et IIB-428Bnzl H 2- Bnzl 0.83 432 C Cbx- Et IIB-429 Bnzl H s-Bu 4-OH-Bnzl 0.88 432C IIB-430 Bnzl H 1- 4-OH-Bnzl 0.97 516 C Npm IIB-431 Bnzl H i-Pr4-OH-Bnzl 0.84 418 C IIB-432 Bnzl H s-Bu 2-Cbx-Et 0.79 398 C IIB-433Bnzl H i-Pr 2-Cbx-Et 0.74 384 C IIB-434 4-OH-Bnzl H i-Pr Bnzl 0.85 418 CIIB-435 4-OH-Bnzl H i-Pr 2-Cbx-Et 0.68 400 C IIB-436 4-OH-Bnzl H i-Pr1-Npm 0.90 468 C IIB-437 2-Cbx-Et H i-Bu Bnzl 0.82 398 C IIB-4382-Cbx-Et H Bnzl Bnzl 0.84 432 C IIB-439 2-Cbx-Et H 4- Bnzl 0.76 448 COH- Bnzl IIB-440 2-Cbx-Et H s-Bu Bnzl 0.81 398 C IIB-441 2-Cbx-Et H 1-Bnzl 0.91 482 C Npm IIB-442 2-Cbx-Et H i-Bu 4-OH-Bnzl 0.76 414 C IIB-4432-Cbx-Et H Bnzl 4-OH-Bnzl 0.78 448 C IIB-444 2-Cbx-Et H s-Bu 4-OH-Bnzl0.75 414 C IIB-445 2-Cbx-Et H 1- 4-OH-Bnzl 0.86 498 C Npm IIB-4462-Cbx-Et H i-Pr 4-OH-Bnzl 0.71 400 C IIB-447 2-Cbx-Et H i-Bu 1-Npm 0.88448 C IIB-448 2-Cbx-Et H 4- 1-Npm 0.83 498 C OH- Bnzl IIB-449 2-Cbx-Et Hs-Bu 1-Npm 0.87 448 C IIB-450 2-Cbx-Et H 1- 1-Npm 0.96 532 C Npm IIB-4511-Npm H 4- Bnzl 0.95 516 C OH- Bnzl IIB-452 1-Npm H Bnzl 4-OH-Bnzl 0.95516 C IIB-453 1-Npm H 2- 4-OH-Bnzl 0.80 498 C Cbx- Et IIB-454 1-Npm Hs-Bu 4-OH-Bnzl 0.94 482 C IIB-455 1-Npm H 1- 4-OH-Bnzl 1.01 566 C NpmIIB-456 1-Npm H i-Pr 4-OH-Bnzl 0.90 468 C IIB-457 1-Npm H i-Bu 2-Cbx-Et0.88 448 C IIB-458 1-Npm H Bnzl 2-Cbx-Et 0.89 482 C IIB-459 1-Npm H 4-2-Cbx-Et 0.81 498 C OH- Bnzl IIB-460 1-Npm H s-Bu 2-Cbx-Et 0.88 448 CIIB-461 1-Npm H 1- 2-Cbx-Et 0.96 532 C Npm IIB-462 1-Npm H 4- 1-Npm0.97, 1.00 566 C * OH- Bnzl IIB-463 1-Npm H 2- 1-Npm 0.93, 0.95 532 C *Cbx- Et IIB-464 i-Bu H 4- i-Bu 0.86 398 C OH- Bnzl IIB-465 i-Bu H 2-i-Bu 0.78 364 C Cbx- Et IIB-466 i-Bu H 1- 3-Gun-Pr 0.78 475 C NpmIIB-467 Bnzl H i-Bu 3-Gun-Pr 0.69 425 C IIB-468 2-Cbx-Et H i-Bu i-Bu0.81 364 C IIB-469 2-Cbx-Et H Bnzl i-Bu 0.83 398 C IIB-470 2-Cbx-Et H 4-i-Bu 0.75 414 C OH- Bnzl IIB-471 2-Cbx-Et H s-Bu i-Bu 0.81 364 C IIB-4722-Cbx-Et H 1- i-Bu 0.91 448 C Npm IIB-473 2-Cbx-Et H i-Pr i-Bu 0.76 350C IIB-474 2-Cbx-Et H Bnzl 1-Npm 0.89 482 C IIB-475 2-Cbx-Et H i-Pr 1-Npm0.84 434 C IIB-476 1-Npm H 3- Bnzl 0.78 509 C Gun- Pr IIB-477 1-Npm Hi-Bu 4-OH-Bnzl 0.94 482 C IIB-478 1-Npm H i-Pr 2-Cbx-Et 0.83 434 CIIB-479 1-Npm H 1- 3-Gun-Pr 0.84 559 C Npm IIB-480 1-Npm H i-Pr 3-Gun-Pr0.72 461 C IIB-481 1-Npm H 3- 1-Npm 0.83 559 C Gun- Pr IIB-482 i-Bu H 3-i-Bu 0.69 391 C Gun- Pr IIB-483 i-Bu H 3- Bnzl 0.70 425 C Gun- PrIIB-484 i-Bu H i-Bu 3-Gun-Pr 0.68 391 C IIB-485 i-Bu H Bnzl 3-Gun-Pr0.71 425 C IIB-486 i-Bu H s-Bu 3-Gun-Pr 0.67 391 C IIB-487 i-Bu H i-Pr3-Gun-Pr 0.63 377 C IIB-488 i-Bu H 3- 1-Npm 0.76 475 C Gun- Pr IIB-489Bnzl H 3- i-Bu 0.71 425 C Gun- Pr IIB-490 Bnzl H 3- Bnzl 0.73 459 C Gun-Pr IIB-491 Bnzl H Bnzl 3-Gun-Pr 0.71 459 C IIB-492 Bnzl H s-Bu 3-Gun-Pr0.68 425 C IIB-493 Bnzl H i-Pr 3-Gun-Pr 0.64 411 C IIB-494 Bnzl H 3-1-Npm 0.78 509 C Gun- Pr IIB-495 2-Cbx-Et H i-Pr Bnzl 0.77 384 C IIB-4963-Gun-Pr H 1-Npm i-Bu 0.79 475 C IIB-497 3-Gun-Pr H i-Pr i-Bu 0.66 377 CIIB-498 3-Gun-Pr H 1-Npm Bnzl 0.79 509 C IIB-499 3-Gun-Pr H i-Pr Bnzl0.66, 0.67 411 C * IIB-500 3-Gun-Pr H 1-Npm 1-Npm 0.82 559 C IIB-5013-Gun-Pr H i-Pr 1-Npm 0.71, 0.74 461 C * IIB-502 1-Npm H 3- i-Bu 0.77475 C Gun- Pr IIB-503 3- H 4-F- 1-Npm 1.05 542 C tertbutoxy- Bnzl propylIIB-504 3- H 4-F- 1-Npm 0.9 486 C hydroxyprop- Bnzl yl IIB-505 Hdr-E H4-Cl- 1-Npm 0.93 488 C Bnzl IIB-506 3- H 3- 3- 1.06 751 C aminopropylamino- amino- propyl propyl IIB-507 1-Npm H β- Ph-Et 0.98 544 C hydroxy-phen- ethyl IIB-508 1-Npm H α- Ph-Et 0.97 558 C (hydroxy- methyl) phen-ethyl IIB-509 1-Npm H α- Ph-Et 1.00 558 C (hydroxy- methyl) phen- ethylIIB-510 4-Nt-Bnzl H Bnzl tBOC-E 0.96 533 C IIB-511 2-OH-Et H Ph-Et 1-Npm0.89 468.3 C IIB-512 Chm H 2-OH- 1-Npm 0.86 460.3 C Et IIB-513 i-Bu Hi-Pr 3-Gun-Pr 0.58 377.3 C IIB-514 Bnzl H 4-OH- i-Bu 0.81 432.2 C BnzlIIB-515 Bnzl H i-Bu 4-OH-Bnzl 0.81 432.2 C IIB-516 i-Bu H Bnzl 4-OH-Bnzl0.81 432.3 C IIB-517 i-Bu H 4-OH- Bnzl 0.81 432.3 C Bnzl IIB-518 2-OH-EtH Bnzl 1-Npm 0.87 454.3 C IIB-519 Ph-Et H 1-Npm Hxy 1.10 508.4 C IIB-5201-Npm H Ph-Et Hxy 1.10 508.4 C IIB-521 Hxy H Ph-Et 1-Npm 1.08 508.4 CIIB-522 Hxy H 1-Npm Ph-Et 1.09 508.4 C IIB-523 i-Pnt H i-Pr i-Bu 3.52348 F IIB-524 Chm H i-Pr i-Bu 3.94 374 F IIB-525 Chm H i-Pr i-Pnt 4.35388 F IIB-526 i-Bu H s-Bu i-Pnt 3.95 362 F IIB-527 i-Pnt H s-Bu i-Bu3.75 362 F IIB-528 i-Pnt H s-Bu Ph-Et 4.29 410 F IIB-529 Chm H s-Bu i-Bu4.22 388 F IIB-530 Chm H s-Bu Ph-Et 4.32 436 F IIB-531 Chm H s-Bu i-Pnt4.52 402 F IIB-532 Chm H i-Pnt i-Bu 4.7 402 F IIB-533 i-Pnt H Hxy i-Bu4.55 390 F IIB-534 2-Cbx-Et H Bnzl 2-OH-Et 2.27 386 F IIB-535 2-Cbx-Et HBnzl i-Pnt 3.49 412 F IIB-536 Ph-Et H Bnzl 2-Cbx-Et 3.02 446 F IIB-5374-F-Bnzl H Bnzl 2-Cbx-Et 3.13 450 F IIB-538 2-OH-Et H Bnzl 2-Cbx-Et 2.52386 F IIB-539 i-Pnt H Bnzl 2-Cbx-Et 3.15 412 F IIB-540 i-Pnt H Bnzl2-OH-Et 3.07 384 F IIB-541 Chm H Bnzl 2-Cbx-Et 3.42 438 F IIB-5422-Cbx-Et H i-Bu Ph-Et 3.3 412 F IIB-543 2-Cbx-Et H i-Bu i-Pnt 3.29 378 FIIB-544 Ph-Et H i-Bu 2-Cbx-Et 3.13 412 F IIB-545 4-F-Bnzl H i-Bu2-Cbx-Et 2.98 416 F IIB-546 2-OH-Et H i-Bu 2-Cbx-Et 3.57 352 G IIB-547i-Pnt H i-Bu 4-OH-Bnzl 3.38 412 F IIB-548 i-Pnt H i-Bu 2-Cbx-Et 2.99 378F IIB-549 Chm H i-Bu 4-OH-Bnzl 3.63 438 F IIB-550 Chm H i-Bu 2-Cbx-Et3.29 404 F IIB-551 2-Cbx-Et H 1-Npm Ph-Et 3.84 496 F IIB-552 2-Cbx-Et H1-Npm 2-OH-Et 2.82 436 F IIB-553 2-Cbx-Et H 1-Npm i-Pnt 3.92 462 FIIB-554 Ph-Et H 1-Npm 2-Cbx-Et 3.72 496 F IIB-555 4-F-Bnzl H 1-Npm2-Cbx-Et 3.62 500 F IIB-556 2-OH-Et H 1-Npm 2-Cbx-Et 2.95 436 F IIB-557i-Pnt H 1-Npm 2-Cbx-Et 3.65 462 F IIB-558 Chm H 1-Npm 2-Cbx-Et 3.94 488F IIB-559 4-OH-Bnzl H i-Pr Ph-Et 3.3 432 F IIB-560 4-OH-Bnzl H i-Pri-Pnt 3.1 398 F IIB-561 2-Cbx-Et H i-Pr Ph-Et 3.04 398 F IIB-5622-Cbx-Et H i-Pr 2-OH-Et 2.82 338 G IIB-563 2-Cbx-Et H i-Pr i-Pnt 3 364 FIIB-564 Ph-Et H i-Pr 2-Cbx-Et 2.87 398 F IIB-565 Ph-Et H i-Pr 2-OH-Et2.82 370 F IIB-566 4-F-Bnzl H i-Pr 2-OH-Et 2.77 374 F IIB-567 2-OH-Et Hi-Pr Bnzl 2.77 356 F IIB-568 2-OH-Et H i-Pr 1-Npm 3.24 406 F IIB-5692-OH-Et H i-Pr 4-OH-Bnzl 2.52 372 F IIB-570 2-OH-Et H i-Pr 2-Cbx-Et 3.09338 G IIB-571 2-OH-Et H i-Pr Ph-Et 3.02 370 F IIB-572 i-Pnt H i-Pr4-OH-Bnzl 3.04 398 F IIB-573 i-Pnt H i-Pr 2-Cbx-Et 2.69 364 F IIB-574i-Pnt H i-Pr 2-OH-Et 2.65 336 F IIB-575 Chm H i-Pr 4-OH-Bnzl 3.34 424 FIIB-576 Chm H i-Pr 2-Cbx-Et 2.94 390 F IIB-577 i-Bu H s-Bu 2-OH-Et 2.62336 F IIB-578 4-OH-Bnzl H s-Bu Ph-Et 3.50 446 F IIB-579 4-OH-Bnzl H s-Bui-Pnt 3.38 412 F IIB-580 2-Cbx-Et H s-Bu Ph-Et 3.22 412 F IIB-5812-Cbx-Et H s-Bu i-Pnt 3.27 378 F IIB-582 Ph-Et H s-Bu 2-Cbx-Et 3.10 412F IIB-583 4-F-Bnzl H s-Bu 2-Cbx-Et 2.88 416 F IIB-584 2-OH-Et H s-Bu4-OH-Bnzl 2.69 386 F IIB-585 2-OH-Et H s-Bu 2-Cbx-Et 3.47 352 G IIB-5862-OH-Et H s-Bu i-Pnt 3.24 350 F IIB-587 i-Pnt H s-Bu 4-OH-Bnzl 3.34 412F IIB-588 i-Pnt H s-Bu 2-Cbx-Et 2.90 378 F IIB-589 i-Pnt H s-Bu 2-OH-Et2.90 350 F IIB-590 Chm H s-Bu 4-OH-Bnzl 3.62 438 F IIB-591 Chm H s-Bu2-Cbx-Et 3.24 404 F IIB-592 i-Bu H 4-OH- i-Pnt 3.52 412 F Bnzl IIB-5932-Cbx-Et H 4-OH- Ph-Et 3.04 462 F Bnzl IIB-594 2-Cbx-Et H 4-OH- i-Pnt2.92 428 F Bnzl IIB-595 Ph-Et H 4-OH- 2-Cbx-Et 2.85 462 F Bnzl IIB-5964-F-Bnzl H 4-OH- 2-Cbx-Et 2.77 466 F Bnzl IIB-597 2-OH-Et H 4-OH-2-Cbx-Et 3.24 402 G Bnzl IIB-598 i-Pnt H 4-OH- 2-Cbx-Et 2.72 428 F BnzlIIB-599 Chm H 4-OH- 2-Cbx-Et 2.97 454 F Bnzl IIB-600 i-Bu H 2- Ph-Et3.12 412 F Cbx- Et IIB-601 i-Bu H 2- i-Pnt 3.12 378 F Cbx- Et IIB-6022-OH-Et H 2- i-Bu 3.5 352 G Cbx- Et IIB-603 i-Pnt H 2- i-Bu 3.04 378 FCbx- Et IIB-604 i-Pnt H 2- 4-OH-Bnzl 2.63 428 F Cbx- Et IIB-605 Chm H 2-i-Bu 3.34 404 F Cbx- Et IIB-606 Chm H 2- 4-OH-Bnzl 2.85 454 F Cbx- EtIIB-607 Chm H 2- i-Pnt 3.59 418 F Cbx- Et IIB-608 Bnzl H 4-F- 4-OH-Bnzl3.63 484 F Bnzl IIB-609 Bnzl H 4-F- 2-Cbx-Et 3.12 450 F Bnzl IIB-610i-Bu H 4-F- 4-OH-Bnzl 3.44 450 F Bnzl IIB-611 i-Bu H 4-F- 2-Cbx-Et 3.02416 F Bnzl IIB-612 1-Npm H 4-F- 4-OH-Bnzl 3.99 534 F Bnzl IIB-613 1-NpmH 4-F- 2-Cbx-Et 3.57 500 F Bnzl IIB-614 4-OH-Bnzl H 4-F- 2-Cbx-Et 2.85466 F Bnzl IIB-615 4-OH-Bnzl H 4-F- Ph-Et 3.63 498 F Bnzl IIB-6164-OH-Bnzl H 4-F- i-Pnt 3.57 464 F Bnzl IIB-617 2-Cbx-Et H 4-F- 4-OH-Bnzl2.95 466 F Bnzl IIB-618 2-Cbx-Et H 4-F- Ph-Et 3.48 464 F Bnzl IIB-6192-Cbx-Et H 4-F- i-Pnt 3.42 430 F Bnzl IIB-620 Ph-Et H 4-F- 4-OH-Bnzl3.67 498 F Bnzl IIB-621 Ph-Et H 4-F- 2-Cbx-Et 3.32 464 F Bnzl IIB-6222-OH-Et H 4-F- 4-OH-Bnzl 2.95 438 F Bnzl IIB-623 2-OH-Et H 4-F- 2-Cbx-Et2.57 404 F Bnzl IIB-624 i-Pnt H 4-F- 4-OH-Bnzl 3.54 464 F Bnzl IIB-625i-Pnt H 4-F- 2-Cbx-Et 3.19 430 F Bnzl IIB-626 Chm H 4-F- 4-OH-Bnzl 3.80490 F Bnzl IIB-627 Chm H 4-F- 2-Cbx-Et 3.45 456 F Bnzl IIB-628 i-Bu Hi-Pnt 2-Cbx-Et 3.05 378 F IIB-629 4-OH-Bnzl H i-Pnt 2-Cbx-Et 2.80 428 FIIB-630 2-Cbx-Et H i-Pnt i-Bu 3.25 378 F IIB-631 2-Cbx-Et H i-Pnt4-OH-Bnzl 2.90 428 F IIB-632 2-OH-Et H i-Pnt i-Bu 3.20 350 F IIB-6332-OH-Et H i-Pnt 2-Cbx-Et 2.59 366 F IIB-634 Chm H i-Pnt 2-Cbx-Et 3.54418 F IIB-635 i-Bu H 2-OH- i-Bu 2.69 336 F Et IIB-636 i-Bu H 2-OH-4-OH-Bnzl 2.35 386 F Et IIB-637 i-Npm H 2-OH- 4-OH-Bnzl 2.94 470 F EtIIB-638 i-Npm H 2-OH- 2-Cbx-Et 2.63 436 F Et IIB-639 4-OH-Bnzl H 2-OH-Bnzl 2.67 420 F Et IIB-640 4-OH-Bnzl H 2-OH- 1-Npm 3.04 470 F Et IIB-6414-OH-Bnzl H 2-OH- Ph-Et 2.75 434 F Et IIB-642 4-OH-Bnzl H 2-OH- i-Pnt2.60 400 F Et IIB-643 2-Cbx-Et H 2-OH- Bnzl 3.60 386 F Et IIB-6442-Cbx-Et H 2-OH- i-Bu 3.40 352 F Et IIB-645 2-Cbx-Et H 2-OH- 1-Npm 2.84436 F Et IIB-646 2-Cbx-Et H 2-OH- Ph-Et 2.57 400 F Et IIB-647 2-Cbx-Et H2-OH- i-Pnt 2.52 366 F Et IIB-648 Ph-Et H 2-OH- 2-Cbx-Et 2.37 400 F EtIIB-649 4-F-Bnzl H 2-OH- 2-Cbx-Et 2.12 404 F Et IIB-650 i-Pnt H 2-OH-i-Bu 2.94 350 F Et IIB-651 i-Pnt H 2-OH- 2-Cbx-Et 3.34 366 F Et IIB-652Chm H 2-OH- i-Bu 3.17 376 F Et IIB-653 Chm H 2-OH- 2-Cbx-Et 2.47 392 FEt IIB-654 Bnzl H Ph-Et 4-OH-Bnzl 3.69 480 F IIB-655 Bnzl H Ph-Et2-Cbx-Et 3.15 446 F IIB-656 i-Bu H Ph-Et 4-OH-Bnzl 3.47 446 F IIB-657i-Bu H Ph-Et 2-Cbx-Et 3.05 412 F IIB-658 1-Npm H Ph-Et 4-OH-Bnzl 4.02530 F IIB-659 1-Npm H Ph-Et 2-Cbx-Et 3.62 496 F IIB-660 4-OH-Bnzl HPh-Et 2-Cbx-Et 2.85 462 F IIB-661 4-OH-Bnzl H Ph-Et i-Pnt 3.74 460 FIIB-662 2-Cbx-Et H Ph-Et 4-OH-Bnzl 3.02 462 F IIB-663 2-Cbx-Et H Ph-Eti-Pnt 3.55 426 F IIB-664 4-F-Bnzl H Ph-Et 4-OH-Bnzl 3.69 498 F IIB-6654-F-Bnzl H Ph-Et 2-Cbx-Et 3.22 464 F IIB-666 2-OH-Et H Ph-Et 4-OH-Bnzl2.99 434 F IIB-667 2-OH-Et H Ph-Et 2-Cbx-Et 2.62 400 F IIB-668 i-Pnt HPh-Et 4-OH-Bnzl 3.63 460 F IIB-669 i-Pnt H Ph-Et 2-Cbx-Et 3.27 426 FIIB-670 Chm H Ph-Et 4-OH-Bnzl 3.92 486 F IIB-671 Chm H Ph-Et 2-Cbx-Et3.55 452 F IIB-672 Bnzl H Hxy 2-Cbx-Et 3.54 426 F IIB-673 i-Bu H Hxy2-Cbx-Et 3.42 392 F IIB-674 1-Npm H Hxy 2-Cbx-Et 4 476 F IIB-6754-OH-Bnzl H Hxy 2-Cbx-Et 3.17 442 F IIB-676 2-Cbx-Et H Hxy i-Bu 3.54 392F IIB-677 2-Cbx-Et H Hxy 4-OH-Bnzl 3.25 442 F IIB-678 2-Cbx-Et H Hxyi-Put 3.84 406 F IIB-679 Ph-Et H Hxy 2-Cbx-Et 3.75 440 F IIB-6804-F-Bnzl H Hxy 2-Cbx-Et 3.6 444 F IIB-681 2-OH-Et H Hxy i-Bu 3.6 364 FIIB-682 2-OH-Et H Hxy 4-OH-Bnzl 3.29 414 F IIB-683 2-OH-Et H Hxy2-Cbx-Et 2.88 380 F IIB-684 2-OH-Et H Hxy i-Pnt 3.87 378 F IIB-685 i-PutH Hxy 4-OH-Bnzl 3.98 440 F IIB-686 i-Put H Hxy 2-Cbx-Et 3.59 406 FIIB-687 i-Put H Hxy 2-OH-Et 3.52 378 F IIB-688 Chm H Hxy 4-OH-Bnzl 4.24466 F IIB-689 Chm H Hxy 2-Cbx-Et 3.88 432 F IIB-690 tBOC-E H Bnzl i-Pnt4.47 468 F IIB-691 Ph-Et H Bnzl tBOC-E 4.34 502 F IIB-692 4-F-Bnzl HBnzl tBOC-E 4.09 506 F IIB-693 2-OtBu-Et H Bnzl tBOC-E 4.27 498 FIIB-694 i-Put H Bnzl tBOC-E 4.25 468 F IIB-695 Chm H Bnzl tBOC-E 4.5 494F IIB-696 tBOC-E H i-Bu Ph-Et 4.25 468 F IIB-697 tBOC-E H i-Bu i-Pnt 4.3434 F IIB-698 Ph-Et H i-Bu tBOC-E 4.18 468 F IIB-699 2-OtBu-Et H i-ButBOC-E 4.09 464 F IIB-700 i-Pnt H i-Bu 4-tBuO- 4.43 468 F Bnzl IIB-701i-Pnt H i-Bu tBOC-E 3.97 434 F IIB-702 Chm H i-Bu 4-tBuO- 4.67 494 FBnzl IIB-703 Chm H i-Bu tBOC-E 4.43 460 F IIB-704 tBOC-E H 1-Npm Ph-Et4.78 552 F IIB-705 tBOC-E H 1-Npm i-Pnt 4.89 518 F IIB-706 Ph-Et H 1-NpmtBOC-E 4.72 552 F IIB-707 4-F-Bnzl H 1-Npm tBOC-E 4.52 556 F IIB-7082-OtBu-Et H 1-Npm tBOC-E 5.37 548 F IIB-709 i-Pnt H 1-Npm tBOC-E 4.68518 F IIB-710 Chm H 1-Npm tBOC-E 4.9 544 F IIB-711 4-tBuO-Bnzl H i-PrPh-Et 4.29 488 F IIB-712 tBOC-E H i-Pr Ph-Et 3.92 454 F IIB-713 tBOC-E Hi-Pr i-Pnt 4 420 F IIB-714 Ph-Et H i-Pr tBOC-E 3.92 454 F IIB-7152-OtBu-Et H i-Pr Bnzl 3.77 412 F IIB-716 2-OtBu-Et H i-Pr 1-Npm 4.24 462F IIB-717 2-OtBu-Et H i-Pr 4-tBuO- 4.37 484 F Bnzl IIB-718 2-OtBu-Et Hi-Pr tBOC-E 3.94 450 F IIB-719 2-OtBu-Et H i-Pr i-Pnt 4.04 392 F IIB-720i-Pnt H i-Pr 4-tBuO- 4.22 454 F Bnzl IIB-721 i-Pnt H i-Pr tBOC-E 4.82420 F IIB-722 Chm H i-Pr 4-tBuO- 4.57 480 F Bnzl IIB-723 4-tBuO-Bnzl Hs-Bu Ph-Et 4.5 502 F IIB-724 4-tBuO-Bnzl H s-Bu i-Pnt 4.62 468 F IIB-725tBOC-E H s-Bu Ph-Et 4.29 468 F IIB-726 tBOC-E H s-Bu i-Pnt 4.3 434 FIIB-727 Ph-Et H s-Bu tBOC-E 4.14 468 F IIB-728 4-F-Bnzl H s-Bu tBOC-E4.52 472 F IIB-729 2-OtBu-Et H s-Bu 4-tBuO- 4.68 498 F Bnzl IIB-7302-OtBu-Et H s-Bu tBOC-E 4.17 464 F IIB-731 i-Pnt H s-Bu 4-tBuO- 4.74 468F Bnzl IIB-732 i-Pnt H s-Bu tBOC-E 4.27 434 F IIB-733 Chm H s-Bu 4-tBuO-4.74 494 F Bnzl IIB-734 i-Bu H 4- i-Pnt 4.57 468 F tBuO- Bnzl IIB-735tBOC-E H 4- Ph-Et 5.2 574 F tBuO- Bnzl IIB-736 tBOC-E H 4- i-Pnt 4.6 540F tBuO- Bnzl IIB-737 Ph-Et H 4- tBOC-E 4.59 574 F tBuO- Bnzl IIB-7384-F-Bnzl H 4- tBOC-E 4.5 578 F tBuO- Bnzl IIB-739 2-OtBu-Et H 4- tBOC-E4.79 570 F tBuO- Bnzl IIB-740 i-Pnt H 4- tBOC-E 4.8 540 F tBuO- BnzlIIB-741 Chm H 4- tBOC-E 4.99 566 F tBuO- Bnzl IIB-742 i-Bu H tBOC- Ph-Et4.12 468 F E IIB-743 i-Bu H tBOC- i-Pnt 4.18 434 F E IIB-744 2-OtBu-Et HtBOC- i-Bu 4.1 464 F E IIB-745 i-Pnt H tBOC- i-Bu 4.17 434 F E IIB-746Chm H tBOC- 4-tBuO- 4.95 566 F E Bnzl IIB-747 Chm H tBOC- i-Pnt 4.55 474F E IIB-748 Bnzl H 4-F- 4-tBuO- 4.54 540 F Bnzl Bnzl IIB-749 Bnzl H 4-F-tBOC-E 4.05 506 F Bnzl IIB-750 i-Bu H 4-F- 4-tBuO- 4.39 506 F Bnzl BnzlIIB-751 i-Bu H 4-F- tBOC-E 3.97 472 F Bnzl IIB-752 1-Npm H 4-F- 4-tBuO-4.92 590 F Bnzl Bnzl IIB-753 1-Npm H 4-F- tBOC-E 4.57 556 F Bnzl IIB-7544-tBuO-Bnzl H 4-F- tBOC-E 4.62 578 F Bnzl IIB-755 4-tBuO-Bnzl H 4-F-Ph-Et 4.6 554 F Bnzl IIB-756 4-tBuO-Bnzl H 4-F- i-Pnt 4.47 520 F BnzlIIB-757 tBOC-E H 4-F- 4-tBuO- 4.74 578 F Bnzl Bnzl IIB-758 tBOC-E H 4-F-Ph-Et 4.24 520 F Bnzl IIB-759 tBOC-E H 4-F- i-Pnt 4.4 486 F Bnzl IIB-760Ph-Et H 4-F- 4-tBuO- 4.59 554 F Bnzl Bnzl IIB-761 Ph-Et H 4-F- tBOC-E4.4 520 F Bnzl IIB-762 2-OtBu-Et H 4-F- 4-tBuO- 4.72 550 F Bnzl BnzlIIB-763 2-OtBu-Et H 4-F- tBOC-E 4.3 516 F Bnzl IIB-764 i-Pnt H 4-F-4-tBuO- 4.57 520 F Bnzl Bnzl IIB-765 i-Pnt H 4-F- tBOC-E 4.22 486 F BnzlIIB-766 Chm H 4-F- 4-tBuO- 4.89 546 F Bnzl Bnzl IIB-767 Chm H 4-F-tBOC-E 4.39 512 F Bnzl IIB-768 i-Bu H i-Pnt tBOC-E 4 434 F IIB-7694-tBuO-Bnzl H i-Pnt tBOC-E 4.77 540 F IIB-770 tBOC-E H i-Pnt i-Bu 4.37434 F IIB-771 tBOC-E H i-Pnt 4-tBuO- 4.79 540 F Bnzl IIB-772 2-OtBu-Et Hi-Pnt i-Bu 4.5 406 F IIB-773 2-OtBu-Et H i-Pnt tBOC-E 4.67 478 F IIB-774i-Bu H 2- i-Bu 3.49 392 F OtBu- Et IIB-775 i-Bu H 2- 4-tBuO- 4.34 498 FOtBu- Bnzl Et IIB-776 i-Bu H 2- tBOC-E 3.74 464 F OtBu- Et IIB-777 1-NpmH 2- 4-tBuO- 4.75 582 F OtBu- Bnzl Et IIB-778 1-Npm H 2- tBOC-E 4.42 548F OtBu- Et IIB-779 4-tBuO-Bnzl H 2- Bnzl 4.42 532 F OtBu- Et IIB-7804-tBuO-Bnzl H 2- 1-Npm 4.82 582 F OtBu- Et IIB-781 4-tBuO-Bnzl H 2-tBOC-E 4.4 570 F OtBu- Et IIB-782 4-tBuO-Bnzl H 2- i-Pnt 4.64 512 FOtBu- Et IIB-783 tBOC-E H 2- Bnzl 3.99 498 F OtBu- Et IIB-784 tBOC-E H2- i-Bu 4.15 464 F OtBu- Et IIB-785 tBOC-E H 2- 4-tBuO- 4.54 570 F OtBu-Bnzl Et IIB-786 tBOC-E H 2- i-Pnt 4.22 478 F OtBu- Et IIB-787 Ph-Et H 2-tBOC-E 4.04 512 F OtBu- Et IIB-788 Chm H 2- i-Bu 4.12 432 F OtBu- EtIIB-789 Chm H 2- tBOC-E 4.32 504 F OtBu- Et IIB-790 Bnzl H Ph-Et 4-tBuO-4.62 536 F Bnzl IIB-791 Bnzl H Ph-Et tBOC-E 4.15 502 F IIB-792 i-Bu HPh-Et 4-tBuO- 4.47 502 F Bnzl IIB-793 i-Bu H Ph-Et tBOC-E 4.09 468 FIIB-794 1-Npm H Ph-Et 4-tBuO- 4.95 586 F Bnzl IIB-795 1-Npm H Ph-EttBOC-E 4.62 552 F IIB-796 4-tBuO-Bnzl H Ph-Et tBOC-E 4.72 574 F IIB-7974-tBuO-Bnzl H Ph-Et i-Pnt 4.74 516 F IIB-798 tBOC-E H Ph-Et i-Pnt 4.65482 F IIB-799 4-F-Bnzl H Ph-Et 4-tBuO- 4.67 554 F Bnzl IIB-800 4-F-BnzlH Ph-Et tBOC-E 4.24 520 F IIB-801 2-OtBu-Et H Ph-Et 4-tBuO- 4.8 546 FBnzl IIB-802 2-OtBu-Et H Ph-Et tBOC-E 4.3 512 F IIB-803 i-Pnt H Ph-Et4-tBuO- 4.67 516 F Bnzl IIB-804 i-Pnt H Ph-Et tBOC-E 4.34 482 F IIB-805Chm H Ph-Et 4-tBuO- 4.93 542 F Bnzl IIB-806 Chm H Ph-Et tBOC-E 4.6 508 FIIB-807 Bnzl H Hxy tBOC-E 4.49 482 F IIB-808 1-Npm H Hxy tBOC-E 5 532 FIIB-809 4-tBuO-Bnzl H Hxy 1-Npm 5.37 566 F IIB-810 4-tBuO-Bnzl H HxytBOC-E 5.05 554 F IIB-811 tBOC-E H Hxy i-Bu 4.75 448 F IIB-812 tBOC-E HHxy 1-Npm 4.92 532 F IIB-813 tBOC-E H Hxy 4-tBuO- 5.04 554 F BnzlIIB-814 tBOC-E H Hxy i-Pnt 5 462 F IIB-815 Ph-Et H Hxy tBOC-E 4.72 496 FIIB-816 4-F-Bnzl H Hxy tBOC-E 4.6 500 F IIB-817 2-OtBu-Et H Hxy 4-tBuO-5.17 526 F Bnzl IIB-818 2-OtBu-Et H Hxy tBOC-E 4.87 492 F IIB-8192-OtBu-Et H Hxy i-Pnt 4.95 434 F IIB-820 i-Pnt H Hxy 4-tBuO- 5.05 496 FBnzl IIB-821 i-Pnt H Hxy tBOC-E 4.7 462 F IIB-822 Chm H Hxy 4-tBuO- 5.29522 F Bnzl IIB-823 i-Bu H i-Bu Ph-Et 3.33 396 H IIB-824 i-Bu H i-Bui-Pnt 3.17 362 H IIB-825 1-Npm H i-Bu i-Pnt 3.45 446 H IIB-826 4-F-BnzlH i-Bu i-Bu 3.03 400 H IIB-827 4-F-Bnzl H i-Bu 1-Npm 3.26 484 H IIB-8284-F-Bnzl H i-Bu Ph-Et 3.15 448 H IIB-829 4-F-Bnzl H i-Bu i-Pnt 3.15 414H IIB-830 i-Pnt H i-Bu i-Bu 3.13 362 H IIB-831 i-Pnt H i-Bu 1-Npm 3.3446 H IIB-832 i-Pnt H i-Bu Ph-Et 3.17 410 H IIB-833 Chm H i-Bu i-Bu 3.26388 H IIB-834 Chm H i-Bu 1-Npm 3.48 472 H IIB-835 Chm H i-Bu Ph-Et 3.32436 H IIB-836 Bnzl H Bnzl Ph-Et 3.39 464 H IIB-837 1-Npm H Bnzl i-Pnt3.37 480 H IIB- Ph-Et H Bnzl 1-Npm 3.4 514 H 838 IIB- Ph-Et H Bnzl i-Pnt3.26 444 H 839 IIB- 4-F-Bnzl H Bnzl 1-Npm 3.34 518 H 840 IIB- 4-F-Bnzl HBnzl Ph-Et 3.17 482 H 841 IIB- 4-F-Bnzl H Bnzl i-Pnt 3.21 448 H 842 IIB-i-Pnt H Bnzl 1-Npm 3.36 480 H 843 IIB- Chm H Bnzl 1-Npm 3.47 506 H 844IIB- Chm H Bnzl Ph-Et 3.33 470 H 845 IIB- Chm H Bnzl i-Pnt 3.37 436 H846 IIB- Bnzl H 1-Npm Ph-Et 3.39 514 H 847 IIB- Bnzl H 1-Npm i-Pnt 3.44480 H 848 IIB- i-Bu H 1-Npm i-Pnt 3.3 446 H 849 IIB- 1-Npm H 1-Npm Ph-Et3.56 564 H 850 IIB- 1-Npm H 1-Npm i-Pnt 3.59 530 H 851 IIB- Ph-Et H1-Npm Bnzl 3.41 514 H 852 IIB- Ph-Et H 1-Npm i-Bu 3.38 480 H 853 IIB-Ph-Et H 1-Npm 1-Npm 3.53 564 H 854 IIB- Ph-Et H 1-Npm i-Pnt 3.46 494 H855 IIB- 4-F-Bnzl H 1-Npm 1-Npm 3.48 568 H 856 IIB- 4-F-Bnzl H 1-NpmPh-Et 3.39 532 H 857 IIB- 4-F-Bnzl H 1-Npm i-Pnt 3.4 498 H 858 IIB-i-Pnt H 1-Npm i-Bu 3.42 446 H 859 IIB- i-Pnt H 1-Npm 1-Npm 3.51 530 H860 IIB- i-Pnt H 1-Npm Ph-Et 3.42 494 H 861 IIB- Chm H 1-Npm Bnzl 3.58506 H 862 IIB- Chm H 1-Npm i-Bu 3.54 472 H 863 IIB- Chm H 1-Npm 1-Npm3.67 556 H 864 IIB- Chm H 1-Npm Ph-Et 3.57 520 H 865 IIB- Chm H 1-Npmi-Pnt 3.59 486 H 866 IIB- Bnzl H i-Pr Ph-Et 3.16 416 H 867 IIB- Bnzl Hi-Pr i-Pnt 3.17 382 H 868 IIB- i-Bu H i-Pr Ph-Et 3.12 382 H 869 IIB-1-Npm H i-Pr Ph-Et 3.34 466 H 870 IIB- 1-Npm H i-Pr i-Pnt 3.38 432 H 871IIB- Ph-Et H i-Pr Bnzl 3.15 416 H 872 IIB- Ph-Et H i-Pr i-Bu 3.12 382 H873 IIB- Ph-Et H i-Pr 1-Npm 3.34 466 H 874 IIB- Ph-Et H i-Pr i-Pnt 3.22396 H 875 IIB- 4-F-Bnzl H i-Pr Bnzl 3.11 420 H 876 IIB- 4-F-Bnzl H i-Pri-Bu 3.04 386 H 877 IIB- 4-F-Bnzl H i-Pr 1-Npm 3.28 470 H 878 IIB-4-F-Bnzl H i-Pr Ph-Et 3.13 434 H 879 IIB- 4-F-Bnzl H i-Pr i-Pnt 3.11 400H 880 IIB- i-Pnt H i-Pr Bnzl 3.08 382 H 881 IIB- i-Pnt H i-Pr 1-Npm 3.31432 H 882 IIB- i-Pnt H i-Pr Ph-Et 3.19 396 H 883 IIB- Chm H i-Pr Bnzl3.27 408 H 884 IIB- Chm H i-Pr 1-Npm 3.45 458 H 885 IIB- Chm H i-PrPh-Et 3.32 422 H 886 IIB- Bnzl H s-Bu Ph-Et 3.22 430 H 887 IIB- Bnzl Hs-Bu i-Pnt 3.25 396 H 888 IIB- i-Bu H s-Bu Ph-Et 3.19 396 H 889 IIB-1-Npm H s-Bu Ph-Et 3.41 480 H 890 IIB- 1-Npm H s-Bu i-Pnt 3.42 446 H 891IIB- Ph-Et H s-Bu Bnzl 3.24 430 H 892 IIB- Ph-Et H s-Bu i-Bu 3.22 396 H893 IIB- Ph-Et H s-Bu 1-Npm 3.39 480 H 894 IIB- Ph-Et H s-Bu i-Pnt 3.32410 H 895 IIB- 4-F-Bnzl H s-Bu Bnzl 3.25 434 H 896 IIB- 4-F-Bnzl H s-Bui-Bu 3.13 400 H 897 IIB- 4-F-Bnzl H s-Bu 1-Npm 3.35 484 H 898 IIB-4-F-Bnzl H s-Bu Ph-Et 3.23 448 H 899 IIB- 4-F-Bnzl H s-Bu i-Pnt 3.25 414H 900 IIB- i-Pnt H s-Bu Bnzl 3.23 396 H 901 IIB- i-Pnt H s-Bu 1-Npm 3.39446 H 902 IIB- Chm H s-Bu Bnzl 3.38 422 H 903 IIB- Chm H s-Bu 1-Npm 3.51472 H 904 IIB- Bnzl H Ph-Et Bnzl 3.24 464 H 905 IIB- Bnzl H Ph-Et 1-Npm3.43 514 H 906 IIB- Bnzl H Ph-Et i-Pnt 3.28 444 H 907 IIB- i-Bu H Ph-Eti-Bu 3.15 396 H 908 IIB- i-Bu H Ph-Et 1-Npm 3.38 480 H 909 IIB- i-Bu HPh-Et i-Pnt 4.41 410 H 910 IIB- 1-Npm H Ph-Et Bnzl 3.47 514 H 911 IIB-1-Npm H Ph-Et i-Bu 3.43 480 H 912 IIB- 1-Npm H Ph-Et 1-Npm 3.58 564 H913 IIB- 4-F-Bnzl H Ph-Et Bnzl 3.23 482 H 914 IIB- 4-F-Bnzl H Ph-Et i-Bu3.17 448 H 915 IIB- 4-F-Bnzl H Ph-Et 1-Npm 3.38 532 H 916 IIB- 4-F-BnzlH Ph-Et i-Pnt 3.26 462 H 917 IIB- i-Pnt H Ph-Et i-Bu 3.24 410 H 918 IIB-i-Pnt H Ph-Et 1-Npm 3.42 494 H 919 IIB- Chm H Ph-Et Bnzl 3.38 470 H 920IIB- Chm H Ph-Et i-Bu 3.33 436 H 921 IIB- Chm H Ph-Et 1-Npm 3.49 520 H922 IIB- Chm H Ph-Et i-Pnt 3.45 450 H 923 IIB- Bnzl H 4-F- Bnzl 3.2 468H 924 Bnzl IIB- Bnzl H 4-F- 1-Npm 3.34 518 H 925 Bnzl IIB- Bnzl H 4-F-Ph-Et 3.2 482 H 926 Bnzl IIB- Bnzl H 4-F- i-Pnt 3.23 448 H 927 Bnzl IIB-i-Bu H 4-F- i-Bu 3.13 400 H 928 Bnzl IIB- i-Bu H 4-F- 1-Npm 3.32 484 H929 Bnzl IIB- i-Bu H 4-F- i-Pnt 3.21 414 H 930 Bnzl IIB- 1-Npm H 4-F-Bnzl 3.47 518 H 931 Bnzl IIB- 1-Npm H 4-F- i-Bu 3.43 484 H 932 Bnzl IIB-1-Npm H 4-F- 1-Npm 3.63 568 H 933 Bnzl IIB- 1-Npm H 4-F- Ph-Et 3.48 532H 934 Bnzl IIB- 1-Npm H 4-F- i-Pnt 3.5 498 H 935 Bnzl IIB- Ph-Et H 4-F-Bnzl 3.28 482 H 936 Bnzl IIB- Ph-Et H 4-F- i-Bu 3.27 448 H 937 Bnzl IIB-Ph-Et H 4-F- 1-Npm 3.42 532 H 938 Bnzl IIB- Ph-Et H 4-F- i-Pnt 3.33 462H 939 Bnzl IIB- i-Pnt H 4-F- 1-Npm 3.33 498 H 940 Bnzl IIB- i-Pnt H 4-F-Ph-Et 3.28 462 H 941 Bnzl IIB- Chm H 4-F- Bnzl 3.31 474 H 942 Bnzl IIB-Chm H 4-F- i-Bu 3.29 440 H 943 Bnzl IIB- Chm H 4-F- 1-Npm 3.47 524 H 944Bnzl IIB- Chm H 4-F- Ph-Et 3.42 488 H 945 Bnzl IIB- Chm H 4-F- i-Pnt3.38 454 H 946 Bnzl IIB- Bnzl H i-Pnt Bnzl 3.27 430 H 947 IIB- Bnzl Hi-Pnt 1-Npm 3.42 480 H 948 IIB- Bnzl H i-Pnt Ph-Et 3.29 444 H 949 IIB-i-Bu H i-Pnt 1-Npm 3.38 446 H 950 IIB- i-Bu H i-Pnt Ph-Et 3.3 410 H 951IIB- 1-Npm H i-Pnt Bnzl 3.45 480 H 952 IIB- 1-Npm H i-Pnt i-Bu 3.42 446H 953 IIB- 1-Npm H i-Pnt 1-Npm 3.56 530 H 954 IIB- Ph-Et H i-Pnt Bnzl3.29 444 H 955 IIB- Ph-Et H i-Pnt i-Bu 3.28 410 H 956 IIB- Ph-Et H i-Pnt1-Npm 3.43 494 H 957 IIB- 4-F-Bnzl H i-Pnt Bnzl 3.27 448 H 958 IIB-4-F-Bnzl H i-Pnt i-Bu 3.2 414 H 959 IIB- 4-F-Bnzl H i-Pnt 1-Npm 3.42 498H 960 IIB- 4-F-Bnzl H i-Pnt Ph-Et 3.28 462 H 961 IIB- Chm H i-Pnt Bnzl3.44 436 H 962 IIB- Chm H i-Pnt 1-Npm 3.58 486 H 963 IIB- Chm H i-PntPh-Et 3.45 450 H 964 IIB- Bnzl H Hxy Bnzl 3.42 444 H 965 IIB- Bnzl H Hxy1-Npm 3.53 494 H 966 IIB- Bnzl H Hxy i-Pnt 3.43 424 H 967 IIB- i-Bu HHxy 1-Npm 3.49 460 H 968 IIB- 1-Npm H Hxy 1-Npm 3.67 544 H 969 IIB-1-Npm H Hxy i-Pnt 3.63 474 H 970 IIB- Ph-Et H Hxy Bnzl 3.43 458 H 971IIB- Ph-Et H Hxy i-Bu 3.39 424 H 972 IIB- Ph-Et H Hxy i-Pnt 3.49 438 H973 IIB- 4-F-Bnzl H Hxy Bnzl 3.41 462 H 974 IIB- 4-F-Bnzl H Hxy i-Bu3.33 428 H 975 IIB- 4-F-Bnzl H Hxy 1-Npm 3.52 512 H 976 IIB- 4-F-Bnzl HHxy Ph-Et 3.4 476 H 977 IIB- 4-F-Bnzl H Hxy i-Pnt 3.42 442 H 978 IIB-i-Pnt H Hxy Bnzl 3.41 424 H 979 IIB- i-Pnt H Hxy 1-Npm 3.58 474 H 980IIB- Chm H Hxy Bnzl 3.54 450 H 981 IIB- Chm H Hxy 1-Npm 3.64 500 H 982IIB- 2-OtBu-Et H i-Bu Bnzl 4.35 426 H 983 IIB- 2-OtBu-Et H i-Bu 1-Npm4.49 476 H 984 IIB- 2-OtBu-Et H Bnzl i-Pnt 4.48 440 H 985 IIB- i-Pnt HBnzl 4-tBuO- 3.42 502 H 986 Bnzl IIB- Chm H Bnzl 4-tBuO- 3.53 528 H 987Bnzl IIB- 4-tBuO-Bnzl H 1-Npm Ph-Et 3.58 586 H 988 IIB- 4-tBuO-Bnzl H1-Npm i-Pnt 3.58 552 H 989 IIB- Ph-Et H 1-Npm 4-tBuO- 3.53 586 H 990Bnzl IIB- 4-F-Bnzl H 1-Npm 4-tBuO- 3.54 590 H 991 Bnzl IIB- 2-OtBu-Et H1-Npm Bnzl 4.52 510 H 992 IIB- 2-OtBu-Et H 1-Npm i-Bu 4.52 476 H 993IIB- 2-OtBu-Et H 1-Npm 1-Npm 4.6 560 H 994 IIB- i-Pnt H 1-Npm 4-tBuO-3.58 552 H 995 Bnzl IIB- Chm H 1-Npm 4-tBuO- 3.69 578 H 996 Bnzl IIB-Bnzl H 4- Ph-Et 3.46 536 H 997 tBuO- Bnzl IIB- Bnzl H 4- i-Pnt 3.46 502H 998 tBuO- Bnzl IIB- i-Bu H 4- Ph-Et 3.42 502 H 999 tBuO- Bnzl IIB-1-Npm H 4- Ph-Et 3.6 586 H 1000 tBuO- Bnzl IIB- 1-Npm H 4- i-Pnt 3.61552 H 1001 tBuO- Bnzl IIB- Ph-Et H 4- Bnzl 3.47 536 H 1002 tBuO- BnzlIIB- Ph-Et H 4- 1-Npm 3.53 586 H 1003 tBuO- Bnzl IIB- Ph-Et H 4- i-Pnt3.53 516 H 1004 tBuO- Bnzl IIB- 4-F-Bnzl H 4- Bnzl 3.39 540 H 1005 tBuO-Bnzl IIB- 4-F-Bnzl H 4- 1-Npm 3.53 590 H 1006 tBuO- Bnzl IIB- 4-F-Bnzl H4- Ph-Et 3.43 554 H 1007 tBuO- Bnzl IIB- 4-F-Bnzl H 4- i-Pnt 3.44 520 H1008 tBuO- Bnzl IIB- 2-OtBu-Et H 4- 1-Npm 3.63 582 H 1009 tBuO- BnzlIIB- i-Pnt H 4- i-Bu 3.38 468 H 1010 tBuO- Bnzl IIB- i-Pnt H 4- 1-Npm3.58 552 H 1011 tBuO- Bnzl IIB- i-Pnt H 4- Ph-Et 3.48 516 H 1012 tBuO-Bnzl IIB- Chm H 4- Bnzl 3.54 528 H 1013 tBuO- Bnzl IIB- Chm H 4- i-Bu3.43 494 H 1014 tBuO- Bnzl IIB- Chm H 4- 1-Npm 3.66 578 H 1015 tBuO-Bnzl IIB- Chm H 4- Ph-Et 3.63 542 H 1016 tBuO- Bnzl IIB- Chm H 4- i-Pnt3.63 508 H 1017 tBuO- Bnzl IIB- Bnzl H tBOC- Ph-Et 3.27 502 H 1018 EIIB- Bnzl H tBOC- i-Pnt 3.25 468 H 1019 E IIB- 1-Npm H tBOC- Ph-Et 3.45552 H 1020 E IIB- 1-Npm H tBOC- i-Pnt 3.47 518 H 1021 E IIB- 4-tBuO-BnzlH tBOC- Ph-Et 3.48 574 H 1022 E IIB- 4-tBuO-Bnzl H tBOC- i-Pnt 3.53 540H 1023 E IIB- Ph-Et H tBOC- Bnzl 3.23 502 H 1024 E IIB- Ph-Et H tBOC-i-Bu 3.29 468 H 1025 E IIB- Ph-Et H tBOC- 1-Npm 3.41 552 H 1026 E IIB-Ph-Et H tBOC- 4-tBuO- 3.47 574 H 1027 E Bnzl IIB- Ph-Et H tBOC- i-Pnt3.32 482 H 1028 E IIB- 4-F-Bnzl H tBOC- Bnzl 3.26 506 H 1029 E IIB-4-F-Bnzl H tBOC- i-Bu 3.21 472 H 1030 E IIB- 4-F-Bnzl H tBOC- 1-Npm 3.42556 H 1031 E IIB- 4-F-Bnzl H tBOC- 4-tBuO- 3.44 578 H 1032 E Bnzl IIB-4-F-Bnzl H tBOC- Ph-Et 3.27 520 H 1033 E IIB- 4-F-Bnzl H tBOC- i-Pnt3.29 486 H 1034 E IIB- 2-OtBu-Et H tBOC- Bnzl 3.34 498 H 1035 E IIB-2-OtBu-Et H tBOC- 1-Npm 3.46 548 H 1036 E IIB- 2-OtBu-Et H tBOC- 4-tBuO-3.52 570 H 1037 E Bnzl IIB- 2-OtBu-Et H tBOC- Ph-Et 3.36 512 H 1038 EIIB- i-Pnt H tBOC- Bnzl 3.25 468 H 1039 E IIB- i-Pnt H tBOC- 1-Npm 3.38518 H 1040 E IIB- i-Pnt H tBOC- Ph-Et 3.27 482 H 1041 E IIB- Chm H tBOC-Bnzl 3.39 494 H 1042 E IIB- Chm H tBOC- 1-Npm 3.54 544 H 1043 E IIB- ChmH tBOC- Ph-Et 3.5 508 H 1044 E IIB- Ph-Et H i-Pr 4-tBuO- 3.36 488 H 1045Bnzl IIB- 4-F-Bnzl H i-Pr 4-tBuO- 3.33 492 H 1046 Bnzl IIB- Ph-Et H s-Bu4-tBuO- 3.43 502 H 1047 Bnzl IIB- 4-F-Bnzl H s-Bu 4-tBuO- 3.46 506 H1048 Bnzl IIB- 2-OtBu-Et H s-Bu Bnzl 3.28 426 H 1049 IIB- 2-OtBu-Et Hs-Bu i-Bu 3.26 392 H 1050 IIB- 2-OtBu-Et H s-Bu 1-Npm 3.48 476 H 1051IIB- 2-OtBu-Et H s-Bu Ph-Et 3.39 440 H 1052 IIB- 4-tBuO-Bnzl H Ph-EtBnzl 3.48 536 H 1053 IIB- 4-tBuO-Bnzl H Ph-Et i-Bu 3.38 502 H 1054 IIB-4-tBuO-Bnzl H Ph-Et 1-Npm 3.58 586 H 1055 IIB- tBOC-E H Ph-Et Bnzl 3.3502 H 1056 IIB- tBOC-E H Ph-Et i-Bu 3.28 468 H 1057 IIB- tBOC-E H Ph-Et1-Npm 3.47 552 H 1058 IIB- 2-OtBu-Et H Ph-Et Bnzl 3.29 474 H 1059 IIB-2-OtBu-Et H Ph-Et i-Bu 3.27 440 H 1060 IIB- 2-OtBu-Et H Ph-Et i-Pnt 3.36454 H 1061 IIB- 4-tBuO-Bnzl H 4-F- Bnzl 3.52 540 H 1062 Bnzl IIB-4-tBuO-Bnzl H 4-F- i-Bu 3.42 506 H 1063 Bnzl IIB- 4-tBuO-Bnzl H 4-F-1-Npm 3.6 590 H 1064 Bnzl IIB- tBOC-E H 4-F- Bnzl 3.27 506 H 1065 BnzlIIB- tBOC-E H 4-F- i-Bu 3.28 472 H 1066 Bnzl IIB- tBOC-E H 4-F- 1-Npm3.45 556 H 1067 Bnzl IIB- 2-OtBu-Et H 4-F- i-Bu 3.22 444 H 1068 BnzlIIB- 2-OtBu-Et H 4-F- Ph-Et 3.33 492 H 1069 Bnzl IIB- 2-OtBu-Et H 4-F-i-Pnt 3.33 458 H 1070 Bnzl IIB- Bnzl H 2- Bnzl 4.32 460 H 1071 OtBu- EtIIB- Bnzl H 2- i-Bu 4.25 426 H 1072 OtBu- Et IIB- Bnzl H 2- 1-Npm 4.42510 H 1073 OtBu- Et IIB- Bnzl H 2- Ph-Et 4.31 474 H 1074 OtBu- Et IIB-Bnzl H 2- i-Pnt 4.34 440 H 1075 OtBu- Et IIB- i-Bu H 2- Bnzl 4.33 426 H1076 OtBu- Et IIB- i-Bu H 2- 1-Npm 4.42 476 H 1077 OtBu- Et IIB- i-Bu H2- Ph-Et 4.35 440 H 1078 OtBu- Et IIB- 1-Npm H 2- Bnzl 4.45 510 H 1079OtBu- Et IIB- 1-Npm H 2- i-Bu 4.48 476 H 1080 OtBu- Et IIB- 1-Npm H 2-Ph-Et 4.48 524 H 1081 OtBu- Et IIB- 1-Npm H 2- i-Pnt 4.53 490 H 1082OtBu- Et IIB- 4-tBuO-Bnzl H 2- i-Bu 4.43 498 H 1083 OtBu- Et IIB- Ph-EtH 2- Bnzl 4.33 474 H 1084 OtBu- Et IIB- Ph-Et H 2- i-Bu 4.33 440 H 1085OtBu- Et IIB- Ph-Et H 2- 1-Npm 4.47 524 H 1086 OtBu- Et IIB- Ph-Et H 2-4-tBuO- 4.49 546 H 1087 OtBu- Bnzl Et IIB- Ph-Et H 2- i-Pnt 4.41 454 H1088 OtBu- Et IIB- 4-F-Bnzl H 2- Bnzl 4.33 478 H 1089 OtBu- Et IIB-4-F-Bnzl H 2- i-Bu 4.26 444 H 1090 OtBu- Et IIB- 4-F-Bnzl H 2- 1-Npm4.43 528 H 1091 OtBu- Et IIB- 4-F-Bnzl H 2- 4-tBuO- 4.47 550 H 1092OtBu- Bnzl Et IIB- 4-F-Bnzl H 2- Ph-Et 4.32 492 H 1093 OtBu- Et IIB-4-F-Bnzl H 2- i-Pnt 4.37 458 H 1094 OtBu- Et IIB- i-Pnt H 2- Bnzl 4.29440 H 1095 OtBu- Et IIB- i-Pnt H 2- 1-Npm 4.43 490 H 1096 OtBu- Et IIB-i-Pnt H 2- 4-tBuO- 4.47 512 H 1097 OtBu- Bnzl Et IIB- Chm H 2- Bnzl 4.43466 H 1098 OtBu- Et IIB- Chm H 2- 4-tBuO- 4.56 538 H 1099 OtBu- Bnzl EtIIB- Chm H 2- Ph-Et 4.46 480 H 1100 OtBu- Et IIB- Bnzl H i-Pnt 4-tBuO-3.43 502 H 1101 Bnzl IIB- Bnzl H i-Pnt tBOC-E 3.23 468 H 1102 IIB- 1-NpmH i-Pnt 4-tBuO- 3.6 552 H 1103 Bnzl IIB- 1-Npm H i-Pnt tBOC-E 3.45 518 H1104 IIB- 4-tBuO-Bnzl H i-Pnt Bnzl 3.48 502 H 1105 IIB- 4-tBuO-Bnzl Hi-Pnt i-Bu 3.47 468 H 1106 IIB- 4-tBuO-Bnzl H i-Pnt 1-Npm 3.64 552 H1107 IIB- 4-tBuO-Bnzl H i-Pnt Ph-Et 3.53 516 H 1108 IIB- tBOC-E H i-PntBnzl 3.33 468 H 1109 IIB- tBOC-E H i-Pnt 1-Npm 3.49 518 H 1110 IIB-tBOC-E H i-Pnt Ph-Et 3.38 482 H 1111 IIB- Ph-Et H i-Pnt 4-tBuO- 3.53 516H 1112 Bnzl IIB- Ph-Et H i-Pnt tBOC-E 3.34 482 H 1113 IIB- 4-F-Bnzl Hi-Pnt 4-tBuO- 3.44 520 H 1114 Bnzl IIB- 4-F-Bnzl H i-Pnt tBOC-E 2.47 486H 1115 IIB- Chm H i-Pnt 4-tBuO- 2.82 508 H 1116 Bnzl IIB- Bnzl H Hxy4-tBuO- 2.73 516 H 1117 Bnzl IIB- i-Bu H Hxy 4-tBuO- 2.7 482 H 1118 BnzlIIB- 1-Npm H Hxy 4-tBuO- 2.88 566 H 1119 Bnzl IIB- 4-tBuO-Bnzl H HxyBnzl 2.78 516 H 1120 IIB- 4-tBuO-Bnzl H Hxy Ph-Et 2.83 530 H 1121 IIB-4-tBuO-Bnzl H Hxy i-Pnt 2.85 496 H 1122 IIB- tBOC-E H Hxy Bnzl 2.62 482H 1123 IIB- tBOC-E H Hxy Ph-Et 2.68 496 H 1124 IIB- Ph-Et H Hxy 4-tBuO-2.77 530 H 1125 Bnzl IIB- 4-F-Bnzl H Hxy 4-tBuO- 2.75 534 H 1126 BnzlIIB- 2-OtBu-Et H Hxy Bnzl 2.48 454 H 1127 IIB- 2-OtBu-Et H Hxy 1-Npm2.75 504 H 1128 IIB- 2-OtBu-Et H Hxy Ph-Et 2.68 468 H 1129 ^(†) Ringformed together by R_(2A) and R_(2B) * IIB-410, 416, 420, 462, 463, 499,and 501 are mixtures of conformational isomers. LCMS Compound t_(R) MassMeasurement Yield number Name of compound (min) (M + H)⁺ condition (%)IIB-1 (3S*,3aS*,6R*,7R*,7aS*)-N,7- 1.19 416 B 18 dibenzyl-1-isobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-2 (3S*,3aS*,6R*,7R*,7aS*)-N,1,7- 1.17 348 B 33triisobutyl-1,2,3,6,7,7a- hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IIB-3(3S*,3aS*,6R*,7R*,7aS*)-7- 1.18 382 B 26 benzyl-N,1-diisobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-4 (3S*,3aS*,6R*,7R*,7aS*)-1- 1.17 382 B 40benzyl-N,7-diisobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IIB-5(3S*,3aS*,6R*,7R*,7aS*)-N- 1.18 382 B 36 benzyl-1,7-diisobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-6 (3S*,3aS*,6R*,7R*,7aS*)-1,7- 1.19 416 B 47dibenzyl-N-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IIB-7(3S*,3aS*,6R*,7R*,7aS*)-N,1- 1.19 416 B 35 dibenzyl-7-isobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-8 (3S*,3aS*,6R*,7R*,7aS*)-N,1,7- 1.21 450 B 36tribenzyl-1,2,3,6,7,7a- hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IIB-9(3S*,3aS*,6R*,7R*,7aS*)-N,7- 1.22 430 B 35 dibenzyl-1-isopentyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-10 (3S*,3aS*,6R*,7R*,7aS*)-N,1- 1.22 430 B 27dibenzyl-7-isopentyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IIB-11(3S*,3aS*,6R*,7R*,7aS*)-N- 1.21 430 B 35 benzyl-1-isobutyl-7-phenethyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-12 (3S*,3aS*,6R*,7R*,7aS*)-1- 1.21 430 B 19benzyl-7-isobutyl-N-phenethyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IIB-13(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.22 430 B 39isobutyl-7-(3-methylbenzyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-14(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.21 430 B 37isobutyl-7-(4-methylbenzyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-15(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.22 430 B 20isobutyl-N-(3-methylbenzyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-16(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.23 430 B 30isobutyl-N-(4-methylbenzyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-17(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N- 1.22 450 B 34(3-chlorobenzyl)-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-18(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N- 1.22 450 B 24(4-chlorobenzyl)-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-19(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.28 484 B 27(3,4-dichlorobenzyl)-7-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-20(3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-N- 1.25 484 B 31(3,4-dichlorobenzyl)-7-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-21(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.18 438 B 54isobutyl-N-(2-(naphthalen-1- yl)ethyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2- b]pyridine-3a-carboxamide IIB-23(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.05 488 A 28 isobutyl-N-(4-(tert-butoxy)benzyl)-1,2,3,6,7,7a- hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-24(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.03 466 A 30isobutyl-N-(naphthalen-1- ylmethyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2- b]pyridine-3a-carboxamide IIB-25(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N- 0.79 370 A 20(2-hydroxyethyl)-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-263-((3S*,3aS*,6R*,7R*,7aS*)-7-benzyl- 0.80 398 A 951-isobutyl-1,2,3,6,7,7a-hexahydro- 1H-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide)propanoic acid IIB-27(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 0.98 454 A 11isobutyl-N-(2-(tert-butoxy)-2- oxoethyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2- b]pyridine-3a-carboxamide IIB-28(3S*,3aS*,6R*,7R*,7aS*)-N-(3-amino- 0.79 397 A 803-oxopropyl)-7-benzyl-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-29(3S*,3aS*,6R*,7R*,7aS*)-N-(4- 0.71 397 A 93aminobutyl)-7-benzyl-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-30(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 0.97 497 A 18 isobutyl-N-(4-((tert-butoxycarbonyl)amino)butyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-31(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N- 1.04 422 A 5cyclohexylmethyl-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-32(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 0.93 424 A 38isobutyl-N-((tetrahydro-2H-pyran- 2-yl)methyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-34(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 0.99 497 A 36 isobutyl-7-(4-((tert-butoxycarbonyl)amino)butyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-36(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 0.89 412 A 22isobutyl-7-(3-methoxy-3- oxopropyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2- b]pyridine-3a-carboxamide IIB-38(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-7- 1.05 422 A 59(cyclohexylmethyl)-1-isobutyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-39(3S*,3aS*,6R*,7R*,7aS*)-N,7- 1.04 456 A 12 dibenzyl-1-cyclohexylmethyl-1,2,3,6,7,7a-hexahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-40 (3S*,3aS*,6R*,7R*,7aS*)-N,7- 0.91 466 A 92dibenzyl-1-(4-hydroxybenzyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-41(3S*,3aS*,6R*,7R*,7aS*)-N,7- 1.05 522 A 10 dibenzyl-1-(4-(tert-butoxy)benzyl)-1,2,3,6,7,7a- hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-42(3S*,3aS*,6R*,7R*,7aS*)-N,7- 1.04 500 A 4 dibenzyl-1-(naphthalen-1-ylmethyl)-1,2,3,6,7,7a-hexahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIB-76 tert-butyl 3- 0.83 488 B 34((3S*,3aS*,6R*,7R*,7aS*)-7-benzyl- 3a-(benzylcarbamoyl)-2,3,3a,6,7,7a-hexahydro-1H-3,6- methanopyrrolo[3,2-b]pyridin-1-yl)propanoate IIB-77 (3S*,3aS*,6R*,7R*,7aS*)-N,1- 0.85 466 B 34dibenzyl-7-(4-hydroxybenzyl)- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IIB-78 tert-butyl 3- 1.00527 B 49 ((3S*,3aS*,6R*,7R*,7aS*)-2-(7- benzyl-1-methyl-2,3,3a,6,7,7a-hexahydro-1H-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide)ethyl)-1H-indole-1- carboxylate IIB-80(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 0.95 452 A 9(naphthalen-1-ylmethyl)-7-propyl- 1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide

TABLE 2

Com- Raw Raw pound Synthesis material material number R₁ R₂ R₃ methodIntermediate 1 2 IIF-1 i-Bu Bnzl Bnzl EX INT-Bnzl SM1-iBu SM2-Ph IIF-2i-Bu i-Bu i-Bu IIB-1, INT-iBu SM1-iBu SM2-Pnt IIF-1 IIF-3 i-Bu i-Bu BnzlIIB-1, INT-iBu SM1-iBu SM2-Ph IIF-1 IIF-4 Bnzl i-Bu i-Bu IIB-1, INT-iBuSM1-Bnzl SM2-Pnt IIF-1 IIF-5 i-Bu Bnzl i-Bu IIB-1, INT-Bnzl SM1-iBuSM2-Pnt IIF-1 IIF-6 Bnzl i-Bu Bnzl IIB-1, INT-iBu SM1-Bnzl SM2-Ph IIF-1IIF-7 Bnzl Bnzl i-Bu IIB-1, N-(benzyl- SM1-Bnzl SM2-Pnt IIF-1 1,2,4-triazine-3- carboxamide IIF-8 Bnzl Bnzl Bnzl IIB-1, INT-Bnzl SM1-BnzlSM2-Ph IIF-1 IIF-9 i- Bnzl Bnzl IIB-1, INT-Bnzl N-allyl-3- SM2-Ph PntIIF-1 methylbutan- 1-amine IIF-10 Bnzl Bnzl i- IIB-1, INT-Bnzl SM1-Bnzl5- Pnt IIF-1 methyl- hexanal IIF-11 i-Bu Bnzl Ph- IIB-1, INT-BnzlSM1-iBu 4- Et IIF-1 phenyl- butanal IIF-12 i-Bu Ph- Bnzl IIB-1, N-SM1-iBu SM2-Ph Et IIF-1 phenethyl- 1,2,4- triazine-3- carboxamide IIF-13i-Bu Bnzl 3- IIB-1, INT-Bnzl SM1-iBu 3-(m- Me- IIF-1 tolyl) Bnzlpropanal IIF-14 i-Bu Bnzl 4- IIB-1, INT-Bnzl SM1-iBu 3-(p- Me- IIF-1tolyl) Bnzl propanal IIF-15 i-Bu 3- Bnzl IIB-1, N-(3- SM1-iBu SM2-Ph Me-IIF-1 methylbenzyl)- Bnzl 1,2,4- triazine-3- carboxamide IIF-16 i-Bu 4-Bnzl IIB-1, N-(4- SM1-iBu SM2-Ph Me- IIF-1 methylbenzyl)- Bnzl 1,2,4-triazine-3- carboxamide IIF-17 i-Bu 3- Bnzl IIB-1, N-(3- SM1-iBu SM2-PhCl- IIF-1 chlorobenzyl)- Bnzl 1,2,4- triazine-3- carboxamide IIF-18 i-Bu4- Bnzl IIB-1, N-(4- SM1-iBu SM2-Ph Cl- IIF-1 chlorobenzyl)- Bnzl 1,2,4-triazine-3- carboxamide IIF-19 3,4- Bnzl i-Bu IIB-1, INT-Bnzl N-(3,4-SM2-Pnt Cl₂- IIF-1 dichlorobenzyl) Bnzl prop-2- en-1-amine IIF-20 Bnzl3,4- i-Bu IIB-1, N-(3,4- SM1-Bnzl SM2-Pnt Cl₂- IIF-1 dichlorobenzyl)-Bnzl 1,2,4- triazine-3- carboxamide IIF-23 i-Bu 4- Bnzl IIB-1,N-(4-tert- SM1-iBu SM2-Ph (tert- IIF-1 butoxybenzyl)- butoxy) 1,2,4-benzyl triazine-3- carboxamide IIF-24 i-Bu Np-M Bnzl IIB-1, N- SM1-iBuSM2-Ph IIF-1 ((naphthalen- 1- yl)methyl)- 1,2,4- triazine-3- carboxamideIIF-25 i-Bu Hdr- Bnzl IIB-1, N-(2- SM1-iBu SM2-Ph E IIF-1 hydroxyethyl)-1,2,4- triazine-3- carboxamide IIF-26 i-Bu Cbx- Bnzl EX IIB-27 E IIF-27i-Bu 2- Bnzl IIB-1, tert-butyl SM1-iBu SM2-Ph (tert- IIF-1 3-(1,2,4-butoxy)- triazine-3- 2-oxo- carboxamide) ethyl propanoate IIF-28 i-BuCbm- Bnzl IIB-28 IIF-26 E IIF-29 i-Bu 4- Bnzl IIB-29 IIF-30 amino- but-yl IIF-30 i-Bu 4- Bnzl IIB-1, tert-butyl SM1-iBu SM2-Ph ((tert- IIF-14-(1,2,4- butoxy- triazine-3- carbon- carboxamide) yl) butyl- aminocarbamate butyl IIF-31 i-Bu Chm Bnzl IIB-1, N- SM1-iBu SM2-Ph IIF-1(cyclohexyl methyl)- 1,2,4- triazine-3- carboxamide IIF-32 i-Bu (tetra-Bnzl IIB-1, N- SM1-iBu SM2-Ph hydro- IIF-1 ((tetrahydro- 2H- 2H-pyran-pyran- 2- 2- yl)methyl)- yl) 1,2,4- methyl triazine-3- carboxamideIIF-34 i-Bu Bnzl 4- IIB-1, INT-Bnzl SM1-iBu tert- ((tert- IIF-1 butyl 5-butoxy- formyl- carbon- pentyl- yl) carba- amino) mate butyl IIF-36 i-BuBnzl 3- IIB-1, INT-Bnzl SM1-iBu methyl meth- IIF-1 4- oxy- formyl- 3-butan- oxo- oate propyl IIF-38 i-Bu Bnzl Chm IIB-1, INT-Bnzl SM1-iBu 3-IIF-1 cyclo- hexyl- propanal IIF-39 Chm Bnzl Bnzl IIB-1, INT-Bnzl N-SM2-Ph IIF-1 (cyclohexyl- methyl)prop- 2-en-1-amine IIF-40 4- Bnzl BnzlIF-40 IIF-41 OH- Bnzl IIF-41 4- Bnzl Bnzl IIB-1, INT-Bnzl N-(4-tert-SM2-Ph (tert- IIF-1 butoxybenzyl) butoxy) prop-2-en- benzyl 1-amineIIF-42 Np-M Bnzl Bnzl IIB-1, INT-Bnzl N- SM2-Ph IIF-1 ((naphthalen- 1-yl)methyl) prop-2-en-1- amine IIF-76 3- Bnzl Bnzl IIB-1, N-benzyl-N-(3-(tert- SM2-Ph (tert- IIF-1 1,2,4- butoxy)-3- butoxy)- triazine-3-oxopropyl)- 3- carboxamide prop-2-en-1- oxo- amine propyl IIF-77 BnzlBnzl 4- IIB-1, N-benzyl- SM1-Bnzl 3-(4- OH- IIF-1 1,2,4- hydroxy- Bnzltriazine-3- phenyl) carboxamide propanal IIF-80 Np-M Bnzl Pr IIB-1,N-benzyl N- pentanal IIF-1 1,2,4- ((naphthalen- triazine-3- 1-carboxamide yl)methyl) prop-2-en-1- amine Com- LCMS Measure- pound tRMass ment number R1 R2 R3 (min) (M + H)⁺ condition IIF-81 benzylnaphthalen- isobutyl 1.29 467 B 1-ylmethyl IIF-82 benzyl 4-(trifluoro-isobutyl 1.29 484 B methyl) benzyl IIF-83 4-chloro- benzyl isobutyl 1.29450 B benzyl IIF-84 3-chloro- benzyl isobutyl 1.30 450 B benzyl IIF-854-methoxy- benzyl isobutyl 1.23 446 B benzyl IIF-86 4-methyl- benzylisobutyl 1.24 430 B benzyl IIF-88 isobutyl isobutyl 4-chloro- 1.26 416 Bbenzyl IIF-89 isobutyl 4-chloro- isobutyl 1.22 416 B benzyl IIF-90isobutyl benzyl isopentyl 1.23 396 B IIF-91 isopentyl benzyl isobutyl1.26 396 B IIF-92 isobutyl isopentyl benzyl 1.23 396 B IIF-93 4-hydroxy-benzyl isobutyl 1.19 432 B benzyl IIF-94 4-(dimethyl- benzyl isobutyl1.27 459 B amino) benzyl IIF-95 4-(tert- benzyl isobutyl 1.29 472 Bbutyl) benzyl IIF-96 4-(trifluoro- benzyl isobutyl 1.32 500 B methoxy)benzyl IIF-97 4-ethoxy benzyl isobutyl 1.25 460 B benzyl IIF-98isopentyl isobutyl benzyl 1.22 396 B IIF-99 benzyl 4-hydroxy- isobutyl1.17 432 B benzyl IIF-100 4-methoxy- 4-hydroxy- isobutyl 1.17 462 Bbenzyl benzyl IIF-101 4-hydroxy- benzyl isopentyl 1.20 446 B benzylIIF-102 benzyl naphthalen- isobutyl 1.27 466 B 2-ylmethyl IIF-103isopentyl 4-chloro- isobutyl 1.28 431 B benzyl IIF-104 isopentyl4-fluoro- isobutyl 1.26 414 B benzyl IIF-105 benzyl pyridin-4- isobutyl1.06 417 B ylmethyl IIF-106 4-methoxy- benzyl benzyl 0.93 480 C benzylIIF-107 phenethyl benzyl 2-(tert- 1.08 532 C butyl- dimethyl- silyloxy)ethyl IIF-109 4-nitro- 4-(tert- 2-(tert- 1.00 605 C benzyl butoxy)butoxy benzyl carbonyl) ethyl IIF-110 i-Bu i-Pr Bnzl 2.92 368 F IIF-111i-Bu i-Bu 4-tBuO- 3.64 454 F Bnzl IIF-112 i-Bu Bnzl 4-tBuO- 3.75 488 FBnzl IIF-113 i-Bu tBOC-E 4-tBuO- 3.73 526 F Bnzl IIF-114 i-Bu s-Bu4-tBuO- 3.64 454 F Bnzl IIF-115 i-Bu 1-Npm 4-tBuO- 4.18 538 F BnzlIIF-116 i-Bu i-Pr 4-tBuO- 3.4 440 F Bnzl IIF-117 i-Bu 1-Npm tBOC-E 3.92504 F IIF-118 i-Bu 1-Npm 1-Npm 4.25 516 F IIF-119 i-Bu i-Pr 1-Npm 3.4418 F IIF-120 Bnzl 4-tBuO-Bnzl Bnzl 3.95 522 F IIF-121 Bnzl i-Bu 4-tBuO-3.79 488 F Bnzl IIF-122 Bnzl Bnzl 4-tBuO- 3.91 522 F Bnzl IIF-123 BnzltBOC-E 4-tBuO- 3.94 560 F Bnzl IIF-124 Bnzl Bnzl tBOC-E 3.47 488 FIIF-125 Bnzl 4-tBuO-Bnzl tBOC-E 3.98 560 F IIF-126 Bnzl 1-Npm tBOC-E3.96 538 F IIF-127 Bnzl i-Bu 1-Npm 3.74 466 F IIF-128 Bnzl Bnzl 1-Npm3.92 500 F IIF-129 Bnzl 4-tBuO-Bnzl 1-Npm 4.27 572 F IIF-130 Bnzl tBOC-E1-Npm 3.8 538 F IIF-131 Bnzl s-Bu 1-Npm 3.74 466 F IIF-132 Bnzl 1-Npm1-Npm 4.31 550 F IIF-133 4-tBuO- Bnzl Bnzl 4.1 522 F Bnzl IIF-1344-tBuO- tBOC-E Bnzl 3.6 560 F Bnzl IIF-135 4-tBuO- s-Bu Bnzl 3.47 488 FBnzl IIF-136 4-tBuO- 1-Npm Bnzl 4.75 572 F Bnzl IIF-137 4-tBuO- BnzltBOC-E 3.69 560 F Bnzl IIF-138 4-tBuO- 1-Npm tBOC-E 4.04 610 F BnzlIIF-139 4-tBuO- i-Bu 1-Npm 3.82 538 F Bnzl IIF-140 4-tBuO- Bnzl 1-Npm4.68 572 F Bnzl IIF-141 4-tBuO- tBOC-E 1-Npm 3.8 610 F Bnzl IIF-1424-tBuO- s-Bu 1-Npm 3.92 538 F Bnzl IIF-143 4-tBuO- 1-Npm 1-Npm 4.65 622F Bnzl IIF-144 i-Bu 4-tBuO-Bnzl Bnzl 3.87 488 F IIF-145 i-Bu tBOC-E Bnzl3.25 454 F IIF-146 i-Bu s-Bu Bnzl 3.12 382 F IIF-147 i-Bu i-Bu tBOC-E3.19 420 F IIF-148 i-Bu Bnzl tBOC-E 3.37 454 F IIF-149 i-Bu 4-tBuO-BnzltBOC-E 3.93 526 F IIF-150 i-Bu i-Pr tBOC-E 2.93 406 F IIF-151 i-Bu i-Bu1-Npm 3.68 432 F IIF-152 i-Bu Bnzl 1-Npm 3.72 466 F IIF-153 i-Bu4-tBuO-Bnzl 1-Npm 4.24 538 F IIF-154 i-Bu tBOC-E 1-Npm 3.74 504 FIIF-155 Bnzl tBOC-E Bnzl 3.44 488 F IIF-156 Bnzl s-Bu Bnzl 3.24 416 FIIF-157 Bnzl 1-Npm Bnzl 3.87 500 F IIF-158 Bnzl i-Pr Bnzl 3.01 402 FIIF-159 Bnzl s-Bu 4-tBuO- 3.82 488 F Bnzl IIF-160 Bnzl 1-Npm 4-tBuO-4.43 572 F Bnzl IIF-161 Bnzl i-Pr 4-tBuO- 3.51 474 F Bnzl IIF-162 Bnzls-Bu tBOC-E 3.34 454 F IIF-163 Bnzl i-Pr tBOC-E 3.15 440 F IIF-164 Bnzli-Pr 1-Npm 3.5 452 F IIF-165 4-tBuO- i-Pr Bnzl 3.49 474 F Bnzl IIF-1664-tBuO- i-Pr tBOC-E 3.38 512 F Bnzl IIF-167 4-tBuO- i-Pr 1-Npm 3.82 524F Bnzl IIF-168 tBOC-E i-Bu Bnzl 3.5 454 F IIF-169 1-Npm i-Bu Bnzl 3.54466 F IIF-170 1-Npm 4-tBuO-Bnzl Bnzl 3.95 572 F IIF-171 1-Npm s-Bu Bnzl3.52 466 F IIF-172 1-Npm i-Pr Bnzl 3.19 452 F IIF-173 1-Npm Bnzl 4-tBuO-4.3 572 F Bnzl IIF-174 1-Npm tBOC-E 4-tBuO- 3.95 610 F Bnzl IIF-1751-Npm s-Bu 4-tBuO- 3.87 538 F Bnzl IIF-176 1-Npm 1-Npm 4-tBuO- 4.62 622F Bnzl IIF-177 1-Npm i-Pr 4-tBuO- 3.84 524 F Bnzl IIF-178 1-Npm BnzltBOC-E 3.8 538 F IIF-179 1-Npm 4-tBuO-Bnzl tBOC-E 4.5 610 F IIF-1801-Npm s-Bu tBOC-E 3.62 504 F IIF-181 1-Npm 1-Npm tBOC-E 4.15 588 FIIF-182 1-Npm Bnzl 1-Npm 4.3 550 F IIF-183 1-Npm 4-tBuO-Bnzl 1-Npm 4.75622 F IIF-184 1-Npm tBOC-E 1-Npm 4.02 588 F IIF-185 1-Npm s-Bu 1-Npm4.25 516 F IIF-186 i-Bu 4-tBuO-Bnzl i-Bu 3.68 454 F IIF-187 i-Bu tBOC-Ei-Bu 3.05 420 F IIF-188 i-Bu s-Bu i-Bu 2.84 348 F IIF-189 i-Bu 1-Npmi-Bu 3.71 432 F IIF-190 i-Bu i-Pr i-Bu 2.66 334 F IIF-191 i-Bu(tBOC)Gun- 4-tBuO- 2.71 641 J Pr Bnzl IIF-192 i-Bu 1-Npm (tBOC)Gun- 3.47675 J Pr IIF-193 i-Bu s-Bu 1-Npm 3.64 432 F IIF-194 Bnzl 4-tBuO-Bnzli-Bu 3.93 488 F IIF-195 Bnzl i-Pr i-Bu 3.01 368 F IIF-196 Bnzl i-ButBOC-E 3.32 454 F IIF-197 tBOC-E Bnzl i-Bu 3.52 454 F IIF-198 tBOC-E4-tBuO-Bnzl i-Bu 4.01 526 F IIF-199 tBOC-E s-Bu i-Bu 3.26 420 F IIF-200tBOC-E 1-Npm i-Bu 4.09 504 F IIF-201 tBOC-E i-Pr i-Bu 3.03 406 F IIF-202tBOC-E 1-Npm Bnzl 4.06 538 F IIF-203 tBOC-E Bnzl 4-tBuO- 4.19 560 F BnzlIIF-204 tBOC-E 1-Npm 4-tBuO- 4.62 610 F Bnzl IIF-205 tBOC-E i-Bu 1-Npm3.96 504 F IIF-206 tBOC-E 4-tBuO-Bnzl 1-Npm 4.41 610 F IIF-207 tBOC-E1-Npm 1-Npm 4.48 588 F IIF-208 tBOC-E i-Pr 1-Npm 3.71 490 F IIF-2091-Npm i-Bu i-Bu 3.32 432 F IIF-210 1-Npm Bnzl i-Bu 3.38 466 F IIF-2111-Npm 4-tBuO-Bnzl i-Bu 3.67 538 F IIF-212 1-Npm s-Bu i-Bu 3.35 432 FIIF-213 1-Npm 1-Npm i-Bu 3.8 516 F IIF-214 1-Npm i-Pr i-Bu 3.17 418 FIIF-215 1-Npm i-Bu 4-tBuO- 3.92 538 F Bnzl IIF-216 1-Npm i-Bu tBOC-E 3.5504 F IIF-217 1-Npm i-Pr tBOC-E 3.34 490 F IIF-218 1-Npm i-Bu 1-Npm 3.79516 F IIF-219 1-Npm (tBOC)Gun- 1-Npm 3.82 759 F Pr IIF-220 1-Npm i-Pr1-Npm 3.65 502 F IIF-221 i-Bu (tBOC)Gun- i-Bu 2.89 591 J Pr IIF-222 i-Bu(tBOC)Gun- Bnzl 2.96 625 J Pr IIF-223 i-Bu s-Bu tBOC-E 3.13 420 FIIF-224 i-Bu i-Bu (tBOC)Gun- 2.96 591 J Pr IIF-225 i-Bu Bnzl (tBOC)Gun-3 625 J Pr IIF-226 i-Bu 4-tBuO-Bnzl (tBOC)Gun- 2.78 641 J Pr IIF-227i-Bu s-Bu (tBOC)Gun- 2.95 591 J Pr IIF-228 i-Bu i-Pr (tBOC)Gun- 2.81 577J Pr IIF-229 i-Bu (tBOC)Gun- 1-Npm 3.08 675 J Pr IIF-230 Bnzl (tBOC)Gun-i-Bu 2.93 625 J Pr IIF-231 Bnzl s-Bu i-Bu 3.23 382 F IIF-232 Bnzl(tBOC)Gun- Bnzl 2.94 659 J Pr IIF-233 Bnzl (tBOC)Gun- 4-tBuO- 2.74 675 JPr Bnzl IIF-234 Bnzl i-Bu (tBOC)Gun- 3.49 698? J Pr IIF-235 Bnzl Bnzl(tBOC)Gun- 3.18 659 J Pr IIF-236 Bnzl 4-tBuO-Bnzl (tBOC)Gun- 2.95 675 JPr IIF-237 Bnzl s-Bu (tBOC)Gun- 3.04 625 J Pr IIF-238 Bnzl 1-Npm(tBOC)Gun- 4.09 709 J Pr IIF-239 Bnzl (tBOC)Gun- 1-Npm 3.36 709 J PrIIF-240 tBOC-E i-Bu i-Bu 3.25 420 F IIF-241 tBOC-E Bnzl Bnzl 3.62 488 FIIF-242 tBOC-E 4-tBuO-Bnzl Bnzl 4.1 560 F IIF-243 tBOC-E s-Bu Bnzl 4.48454 F IIF-244 tBOC-E i-Pr Bnzl 3.24 440 F IIF-245 tBOC-E i-Bu 4-tBuO-4.15 526 F Bnzl IIF-246 tBOC-E i-Pr 4-tBuO- 3.89 512 F Bnzl IIF-247tBOC-E Bnzl 1-Npm 4.03 538 F IIF-248 tBOC-E s-Bu 1-Npm 3.96 504 FIIF-249 (tBOC)Gun- 1-Npm i-Bu 3.77 657 J Pr IIF-250 (tBOC)Gun- i-Pr i-Bu3.16 577 J Pr IIF-251 (tBOC)Gun- 1-Npm Bnzl 3.71 709 J Pr IIF-252(tBOC)Gun- i-Pr Bnzl 3.18 611 J Pr IIF-253 (tBOC)Gun- 1-Npm 4-tBuO- 3.39725 J Pr Bnzl IIF-254 (tBOC)Gun- i-Pr 4-tBuO- 2.96 627 J Pr Bnzl IIF-255(tBOC)Gun- 1-Npm 1-Npm 3.97 759 J Pr IIF-256 (tBOC)Gun- i-Pr 1-Npm 3.47661 J Pr IIF-257 1-Npm 1-Npm Bnzl 4.5 550 F IIF-258 Bnzl tBOC-E i-Bu3.51 454 F IIF-259 Bnzl i-Pr (tBOC)Gun- 2.99 611 J Pr IIF-260 4-tBuO-i-Bu i-Bu 3.42 454 F Bnzl IIF-261 4-tBuO- Bnzl i-Bu 3.44 488 F BnzlIIF-262 4-tBuO- tBOC-E i-Bu 3.5 526 F Bnzl IIF-263 4-tBuO- (tBOC)Gun-i-Bu 3.29 641 F Bnzl Pr IIF-264 4-tBuO- s-Bu i-Bu 3.45 454 F BnzlIIF-265 4-tBuO- 1-Npm i-Bu 3.9 538 F Bnzl IIF-266 4-tBuO- i-Pr i-Bu 3.24440 F Bnzl IIF-267 4-tBuO- i-Bu Bnzl 3.57 488 F Bnzl IIF-268 4-tBuO-(tBOC)Gun- Bnzl 3.1 675 F Bnzl Pr IIF-269 4-tBuO- i-Bu tBOC-E 3.6 526 FBnzl IIF-270 4-tBuO- s-Bu tBOC-E 3.59 526 F Bnzl IIF-271 4-tBuO- i-Bu(tBOC)Gun- 3.38 641 F Bnzl Pr IIF-272 4-tBuO- Bnzl (tBOC)Gun- 3.72 675 FBnzl Pr IIF-273 4-tBuO- s-Bu (tBOC)Gun- 3.38 641 F Bnzl Pr IIF-2744-tBuO- 1-Npm (tBOC)Gun- 3.79 725 F Bnzl Pr IIF-275 4-tBuO- i-Pr(tBOC)Gun- 3.27 627 F Bnzl Pr IIF-276 4-tBuO- (tBOC)Gun- 1-Npm 3.54 725F Bnzl Pr IIF-277 tBOC-E s-Bu 4-tBuO- 4.09 526 F Bnzl IIF-278 (tBOC)Gun-i-Bu i-Bu 4.24 591 F Pr IIF-279 (tBOC)Gun- Bnzl i-Bu 3.99 625 F PrIIF-280 (tBOC)Gun- 4-tBuO-Bnzl i-Bu 3.51 641 F Pr IIF-281 (tBOC)Gun-s-Bu i-Bu 3.82 591 F Pr IIF-282 (tBOC)Gun- i-Bu Bnzl 4.27 625 F PrIIF-283 (tBOC)Gun- Bnzl Bnzl 4.14 659 F Pr IIF-284 (tBOC)Gun-4-tBuO-Bnzl Bnzl 3.72 675 F Pr IIF-285 (tBOC)Gun- s-Bu Bnzl 3.99 625 FPr IIF-286 (tBOC)Gun- i-Bu 4-tBuO- 3.59 641 F Pr Bnzl IIF-287 (tBOC)Gun-Bnzl 4-tBuO- 4.32 675 F Pr Bnzl IIF-288 (tBOC)Gun- Bnzl 1-Npm 4.57 709 FPr IIF-289 (tBOC)Gun- s-Bu 1-Npm 4.49 675 F Pr IIF-290 1-Npm tBOC-E i-Bu3.35 504 F IIF-291 1-Npm (tBOC)Gun- i-Bu 3.95 675 F Pr IIF-292 1-Npm(tBOC)Gun- Bnzl 3.7 709 F Pr IIF-293 1-Npm (tBOC)Gun- 4-tBuO- 3.3 725 FPr Bnzl IIF-294 1-Npm i-Bu (tBOC)Gun- 3.77 675 F Pr IIF-295 1-Npm Bnzl(tBOC)Gun- 3.82 709 F Pr IIF-296 1-Npm 4-tBuO-Bnzl (tBOC)Gun- 3.6 725 FPr IIF-297 1-Npm s-Bu (tBOC)Gun- 4.15 675 F Pr IIF-298 1-Npm 1-Npm(tBOC)Gun- 4.91 759 F Pr IIF-299 1-Npm i-Pr (tBOC)Gun- 3.5 661 F PrIIF-300 1-Npm tBOC-E Bnzl 3.47 538 F IIF-301 Bnzl i-Pr 3-Gun-Pr 1.47 411F IIF-302 4-OH-Bnzl i-Pr 3-Gun-Pr 1.37 427 F IIF-303 1-Npm 3-Gun-Pr i-Bu2.75 475 F IIF-304 1-Npm i-Bu 3-Gun-Pr 2.6 475 F IIF-305 1-Npm Bnzl3-Gun-Pr 2.69 509 F IIF-306 1-Npm i-Pr 3-Gun-Pr 2.49 461 F IIF-307 BnzlPh-Et i-Bu 0.93 430 C IIF-308 Chm i-Bu Bnzl 0.97 422 C IIF-309 Bnzl4-F-Bnzl i-Bu 0.93 434 C IIF-310 Chm Bnzl i-Bu 0.97 422 C IIF-311 BnzlHxy i-Bu 1.02 410 C IIF-312 Ph-Et i-Bu i-Bu 0.94 396 C IIF-313 Ph-Eti-Bu 1-Npm 1.01 480 C IIF-314 Bnzl i-Bu Ph-Et 0.97 430 C IIF-3154-F-Bnzl i-Bu Bnzl 0.94 434 C IIF-316 i-Bu 4-F-Bnzl Bnzl 0.93 434 CIIF-317 Ph-Et Bnzl i-Bu 0.94 430 C IIF-318 Bnzl i-Pnt i-Bu 0.96 396 CIIF-319 i-Bu Hxy Bnzl 0.98 410 C IIF-320 4-F-Bnzl Bnzl Bnzl 0.94 468 CIIF-321 Ph-Et Bnzl Bnzl 0.96 464 C IIF-322 Bnzl i-Bu i-Pnt 0.97 396 CIIF-323 4-F-Bnzl Bnzl i-Bu 0.94 434 C

Com- LCMS Measure- pound RT Mass ment number R₁ R_(2A) R_(2B) R₃ (min)(M + H)⁺ condition IIF-324 2- H Bnzl i-Bu 2.89 466 B1 Npm IIF-325 i- H3-Cl-Bnzl Bnzl 2.85 464 B1 Pnt IIF-326 i- H 4-Cl-Bnzl Bnzl 2.85 464 B1Pnt IIF-327 i- H 4-F-Bnzl Bnzl 2.73 448 B1 Pnt IIF-328 i- H 4-Me-BnzlBnzl 2.83 444 B1 Pnt IIF-329 i- H 4-MeO- Bnzl 2.71 460 B1 Pnt BnzlIIF-330 i-Bu H 4-Cl-Bnzl Ph-Et 2.68 464 B1 IIF-331 i-Bu H 3-Cl-BnzlPh-Et 2.85 464 B1 IIF-332 i-Bu H 4-MeO- Ph-Et 2.50 460 B1 Bnzl IIF-333i-Bu H 4-Me-Bnzl Ph-Et 2.65 444 B1 IIF-334 i-Bu H 2-Npm Ph-Et 2.77 480B1 IIF-335 i-Bu H Bnzl Ph-Pr 2.65 444 B1 IIF-336 i-Bu H 3-Cl-Bnzl Ph-Pr1.27 478 B IIF-337 i-Bu H 3-F-Bnzl Ph-Pr 1.25 462 B IIF-338 Cpm H4-OH-Bnzl Cbx-E 0.96 440 B IIF-339 i-Bu H 3-Me-Bnzl Ph-Pr 1.26 458 BIIF-340 i-Bu H 3-MeO- Ph-Pr 1.25 474 B Bnzl IIF-341 i-Bu H 3-Cl-BnzlPh-Bu 1.30 492 B IIF-342 i-Bu H 3-F-Bnzl Ph-Bu 1.26 476 B IIF-343 i-Bu H3-Me-Bnzl Ph-Bu 1.29 472 B IIF-344 i-Bu H 3-MeO- Ph-Bu 1.26 488 B BnzlIIF-345 i-Bu H Bnzl Ph-Bu 1.25 458 B IIF-346 i- H 3-F-Bnzl Ph-Pr 1.25476 B Pnt IIF-347 Hdr- H 4- 1-Npm 0.9 486 C E fluorophen- ethyl IIF-3481- H cyclohexyl Ph-Et 1.02 506 C Npm IIF-349 1- H cyclopentyl Ph-Et 0.99492 C Npm IIF-350 1- H pentyl Ph-Et 1.01 494 C Npm IIF-351 1- H heptylPh-Et 1.08 522 C Npm IIF-352 propyl H Chm Bnzl 0.95 408 C IIF-353 1- Hhexyl 4- 1.07 522 C Npm methylphen- ethyl IIF-354 1- H hexyl 2- 1.10 558C Npm (naphthalen- 2-yl)ethyl IIF-355 1- H hexyl 4- 1.12 550 C Npmisopropylphen- ethyl IIF-356 1- H hexyl cyclohexyl- 1.13 514 C Npm ethylIIF-357 tBuO- H 4- 1-Npm 1.01 542 C E fluorophen- ethyl IIF-358 tBuO- H4-Cl-Bnzl 1-Npm 1.03 545 C E IIF-359 tBuO- H 4-Me-Bnzl 1-Npm 1.02 524 CE IIF-360 1- piperidine ^(†) Ph-Et 0.95 492 C Npm IIF-361 1- pyrrolidine^(†) Ph-Et 0.93 478 C Npm IIF-362 prop- H Bnzl Chm 0.94 408 C yl IIF-363prop- H 2- Bnzl 0.91 416 C yl methyl- benzyl IIF-364 prop- H (1,2,3,4-Bnzl 0.97 456 C yl tetrahydro- naphthalen- 1- yl)methyl IIF-365 prop- HCpm Bnzl 0.92 394 C yl IIF-366 prop- H Bnzl Cpm 0.91 394 C yl IIF-367 1-H Hxy 3- 1.07 522 C Npm methylphen- ethyl IIF-368 4- H Bnzl Bnzl 0.92495 C Nt- Bnzl IIF-369 4- H Hxy Ph-Et 1.01 503 C Nt- Bnzl IIF-370 i- HPh-Et Bnzl 2.76 444 B1 Pnt IIF-371 i- H 1-Npm Bnzl 2.93 480 B1 PntIIF-372 i-Bu H 4-F-Bnzl Ph-Et 2.56 448 B1 IIF-373 i-Bu H Ph-Et Ph-Et2.60 444 B1 IIF-374 i-Bu H 1-Npm Ph-Et 2.79 480 B1 IIF-375 4-F- H 1-NpmBnzl 2.80 518 B1 Bnzl IIF-376 4-F- H 1-Npm i-Bu 1.26 484 B Bnzl IIF-377tBuO- H 4-F-Bnzl 1-Npm 1.01 528 C E IIF-378 4- H Bnzl Ph-Et 1.01 536 CtBuO- Bnzl IIF-379 tBuO- H Bnzl 1-Npm 1.00 510 C E IIF-380 Chm H tBuO-E1-Npm 1.01 516 C IIF-381 tBOC- H Bnzl Ph-Et 0.97 502 C E IIF-382 i- HBnzl Ph-Et 0.96 444 C Pnt IIF-383 1- H 4-F-Bnzl Hdr-E 0.83 472 C NpmIIF-384 Hdr- H 4-F-Bnzl 1-Npm 0.88 472 C E IIF-385 Cbx- H Bnzl Ph-Et0.86 446 C E IIF-386 tBuO- H Ph-Et 1-Npm 1.02 524 C E IIF-387 Ph- H Hxy1-Npm 1.06 508 C Et IIF-388 Ph- H i-Bu TBSO-E 1.09 498 C Et IIF-389 Ph-H i-Bu Hdr-E 0.77 384 C Et IIF-390 Ph- H i-Bu i-Pnt 0.96 410 C EtIIF-391 Ph- H i-Bu 4-tBuO-Bnzl 1.02 502 C Et IIF-392 Ph- H i-Bu4-OH-Bnzl 0.85 446 C Et IIF-393 i-Bu H i-Bu 4-OH-Bnzl 0.80 398 C IIF-394i-Bu H Bnzl 4-OH-Bnzl 0.82 432 C IIF-395 i-Bu H 2-Cbx-Et 4-OH-Bnzl 0.63414 C IIF-396 i-Bu H s-Bu 4-OH-Bnzl 0.79 398 C IIF-397 i-Bu H 1-Npm4-OH-Bnzl 0.89 482 C IIF-398 i-Bu H i-Pr 4-OH-Bnzl 0.75 384 C IIF-399i-Bu H 1-Npm 2-Cbx-Et 0.82 448 C IIF-400 Bnzl H 4-OH- Bnzl 0.83 466 CBnzl IIF-401 Bnzl H i-Bu 4-OH-Bnzl 0.82 432 C IIF-402 Bnzl H 2-Cbx-Et4-OH-Bnzl 0.67 448 C IIF-403 Bnzl H Bnzl 2-Cbx-Et 0.76 432 C IIF-404Bnzl H 4-OH- 2-Cbx-Et 0.68 448 C Bnzl IIF-405 Bnzl H 1-Npm 2-Cbx-Et 0.84482 C IIF-406 Bnzl H 4-OH- 1-Npm 0.89 516 C Bnzl IIF-407 Bnzl H 2-Cbx-Et1-Npm 0.83 482 C IIF-408 4- H 2-Cbx-Et Bnzl 0.69 448 C OH- Bnzl IIF-4094- H s-Bu Bnzl 0.84 432 C OH- Bnzl IIF-410 4- H 1-Npm Bnzl 0.93 516 COH- Bnzl IIF-411 4- H Bnzl 2-Cbx-Et 0.73 448 C OH- Bnzl IIF-412 4- H1-Npm 2-Cbx-Et 0.81 498 C OH- Bnzl IIF-413 4- H i-Bu 1-Npm 0.91 482 COH- Bnzl IIF-414 4- H Bnzl 1-Npm 0.92 516 C OH- Bnzl IIF-415 4- H2-Cbx-Et 1-Npm 0.76 498 C OH- Bnzl IIF-416 4- H s-Bu 1-Npm 0.91 482 COH- Bnzl IIF-417 4- H 1-Npm 1-Npm 0.98 566 C OH- Bnzl IIF-418 i-Bu H4-OH- Bnzl 0.81 432 C Bnzl IIF-419 i-Bu H i-Bu 2-Cbx-Et 0.71 364 CIIF-420 i-Bu H Bnzl 2-Cbx-Et 0.73 398 C IIF-421 i-Bu H 4-OH- 2-Cbx-Et0.65 414 C Bnzl IIF-422 i-Bu H i-Pr 2-Cbx-Et 0.65 350 C IIF-423 i-Bu H4-OH- 1-Npm 0.87 482 C Bnzl IIF-424 i-Bu H 2-Cbx-Et 1-Npm 0.81 448 CIIF-425 Bnzl H 2-Cbx-Et Bnzl 0.76 432 C IIF-426 Bnzl H s-Bu 4-OH-Bnzl0.81 432 C IIF-427 Bnzl H 1-Npm 4-OH-Bnzl 0.90 516 C IIF-428 Bnzl H i-Pr4-OH-Bnzl 0.77 418 C IIF-429 Bnzl H s-Bu 2-Cbx-Et 0.73 398 C IIF-430Bnzl H i-Pr 2-Cbx-Et 0.69 384 C IIF-431 4- H i-Pr Bnzl 0.8 418 C OH-Bnzl IIF-432 4- H i-Pr 2-Cbx-Et 0.65 400 C OH- Bnzl IIF-433 4- H i-Pr1-Npm 0.87 468 C OH- Bnzl IIF-434 2- H i-Bu Bnzl 0.80 398 C Cbx- EtIIF-435 1- H 4-OH- Bnzl 0.89 516 C Npm Bnzl IIF-436 1- H Bnzl 4-OH-Bnzl0.87 516 C Npm IIF-437 1- H 2-Cbx-Et 4-OH-Bnzl 0.73 498 C Npm IIF-438 1-H s-Bu 4-OH-Bnzl 0.86 482 C Npm IIF-439 1- H 1-Npm 4-OH-Bnzl 0.94 566 CNpm IIF-440 1- H i-Pr 4-OH-Bnzl 0.82 468 C Npm IIF-441 1- H Bnzl2-Cbx-Et 0.81 482 C Npm IIF-442 1- H 4-OH- 2-Cbx-Et 0.74 498 C Npm BnzlIIF-443 1- H s-Bu 2-Cbx-Et 0.79 448 C Npm IIF-444 1- H 1-Npm 2-Cbx-Et0.88 532 C Npm IIF-445 1- H 4-OH- 1-Npm 0.96 566 C Npm Bnzl IIF-446 1- H2-Cbx-Et 1-Npm 0.88 532 C Npm IIF-447 i-Bu H 4-OH- i-Bu 0.78 398 C BnzlIIF-448 i-Bu H 2-Cbx-Et i-Bu 0.70 364 C IIF-449 i-Bu H 1-Npm 3-Gun-Pr0.72 475 C IIF-450 Bnzl H i-Bu 2-Cbx-Et 0.73 398 C IIF-451 2- H Bnzli-Bu 0.80 398 C Cbx- Et IIF-452 2- H 4-OH- i-Bu 0.70 414 C Cbx- Bnzl EtIIF-453 2- H s-Bu i-Bu 0.78 364 C Cbx- Et IIF-454 2- H 1-Npm i-Bu 0.88448 C Cbx- Et IIF-455 2- H i-Pr i-Bu 0.74 350 C Cbx- Et IIF-456 2- H1-Npm Bnzl 0.88 482 C Cbx- Et IIF-457 2- H Bnzl 4-OH-Bnzl 0.77 448 CCbx- Et IIF-458 2- H 1-Npm 4-OH-Bnzl 0.84 498 C Cbx- Et IIF-459 2- Hi-Bu 1-Npm 0.86 448 C Cbx- Et IIF-460 2- H 4-OH- 1-Npm 0.77 498 C Cbx-Bnzl Et IIF-461 2- H 1-Npm 1-Npm 0.94 532 C Cbx- Et IIF-462 2- H i-Pr1-Npm 0.82 434 C Cbx- Et IIF-463 1- H 4-OH- i-Bu 0.87 482 C Npm BnzlIIF-464 1- H i-Bu 4-OH-Bnzl 0.85 482 C Npm IIF-465 1- H i-Bu 2-Cbx-Et0.78 448 C Npm IIF-466 1- H i-Pr 2-Cbx-Et 0.75 434 C Npm IIF-467 1- H3-Gun-Pr 1-Npm 0.78 559 C Npm IIF-468 i-Bu H 3-Gun-Pr i-Bu 0.63 391 CIIF-469 i-Bu H 3-Gun-Pr Bnzl 0.66 425 C IIF-470 i-Bu H s-Bu 2-Cbx-Et0.70 364 C IIF-471 i-Bu H i-Bu 3-Gun-Pr 0.62 391 C IIF-472 i-Bu H Bnzl3-Gun-Pr 0.65 425 C IIF-473 i-Bu H s-Bu 3-Gun-Pr 0.62 391 C IIF-474 i-BuH i-Pr 3-Gun-Pr 0.58 377 C IIF-475 i-Bu H 3-Gun-Pr 1-Npm 0.72 475 CIIF-476 Bnzl H 3-Gun-Pr i-Bu 0.67 425 C IIF-477 Bnzl H 3-Gun-Pr Bnzl0.69 459 C IIF-478 Bnzl H i-Bu 3-Gun-Pr 0.64 425 C IIF-479 Bnzl H Bnzl3-Gun-Pr 0.66 459 C IIF-480 Bnzl H s-Bu 3-Gun-Pr 0.64 425 C IIF-481 BnzlH 1-Npm 3-Gun-Pr 0.73 509 C IIF-482 Bnzl H 3-Gun-Pr 1-Npm 0.74 509 CIIF-483 2- H i-Bu i-Bu 0.79 364 C Cbx- Et IIF-484 2- H Bnzl Bnzl 0.81432 C Cbx- Et IIF-485 2- H 4-OH- Bnzl 0.72 448 C Cbx- Bnzl Et IIF-486 2-H s-Bu Bnzl 0.79 398 C Cbx- Et IIF-487 2- H i-Pr Bnzl 0.75 384 C Cbx- EtIIF-488 2- H i-Bu 4-OH-Bnzl 0.75 414 C Cbx- Et IIF-489 2- H i-Pr4-OH-Bnzl 0.70 400 C Cbx- Et IIF-490 2- H Bnzl 1-Npm 0.87 482 C Cbx- EtIIF-491 2- H s-Bu 1-Npm 0.86 448 C Cbx- Et IIF-492 3- H 1-Npm i-Bu 0.79475 C Gun- Pr IIF-493 3- H i-Pr i-Bu 0.67 377 C Gun- Pr IIF-494 3- Hi-Pr Bnzl 0.66 411 C Gun- Pr IIF-495 3- H 1-Npm 1-Npm 0.83 559 C Gun- PrIIF-496 3- H i-Pr 1-Npm 0.73 461 C Gun- Pr IIF-497 3- H 4-F-Bnzl 1-Npm1.00 542 C tert- butoxy- propyl IIF-498 3- H 4-F-Bnzl 1-Npm 0.88 486 Chydroxy- propyl IIF-499 3- H 3- 3- 1.02 751 C amino- amino- aminopropylpropyl propyl IIF-500 1- H β- Ph-Et 0.93 544 C Npm hydroxy- phenethylIIF-501 1- H α- Ph-Et 0.92 558 C Npm (hydroxy- methyl) phenethyl IIF-5021- H α- Ph-Et 0.95 558 C Npm (hydroxy- methyl) phenethyl IIF-503 4- HBnzl tBOC-E 0.93 533 C Nt- Bnzl IIF-504 2- H Ph-Et 1-Npm 0.89 468.3 COH- Et IIF-505 Chm H 2-OH-Et 1-Npm 0.86 460.3 C IIF-506 2- H Bnzl 1-Npm0.87 454.3 C OH- Et IIF-507 Ph- H 1-Npm Hxy 1.06 508.4 C Et IIF-508 1- HPh-Et Hxy 1.04 508.4 C Npm IIF-509 Hxy H Ph-Et 1-Npm 1.04 508.4 CIIF-510 Hxy H 1-Npm Ph-Et 1.03 508.4 C IIF-511 i- H i-Pr i-Bu 3.25 348 FPnt IIF-512 Chm H i-Pr i-Bu 3.49 374 F IIF-513 Chm H i-Pr i-Pnt 3.74 388F IIF-514 i-Bu H s-Bu i-Pnt 3.55 362 F IIF-515 i- H s-Bu i-Bu 3.45 362 FPnt IIF-516 Chm H s-Bu i-Bu 3.72 388 F IIF-517 Chm H s-Bu Ph-Et 4 436 FIIF-518 Chm H s-Bu i-Pnt 4.02 402 F IIF-519 i-Bu H i-Pnt i-Bu 3.52 362 FIIF-520 Chm H i-Pnt i-Bu 3.99 402 F IIF-521 i-Bu H Hxy i-Bu 3.88 376 FIIF-522 Chm H Hxy i-Bu 4.34 416 F IIF-523 2- H Bnzl i-Pnt 3.3 412 F Cbx-Et IIF-524 Ph- H Bnzl 2-Cbx-Et 3.02 446 F Et IIF-525 4-F- H Bnzl2-Cbx-Et 2.85 450 F Bnzl IIF-526 2- H Bnzl 2-Cbx-Et 2.45 386 F OH- EtIIF-527 i- H Bnzl 2-Cbx-Et 2.85 412 F Pnt IIF-528 i- H Bnzl 2-OH-Et 2.84384 F Pnt IIF-529 Chm H Bnzl 2-Cbx-Et 3 438 F IIF-530 2- H i-Bu Ph-Et3.17 412 F Cbx- Et IIF-531 2- H i-Bu i-Pnt 3.12 378 F Cbx- Et IIF-5324-F- H i-Bu 2-Cbx-Et 2.69 416 F Bnzl IIF-533 2- H i-Bu 2-Cbx-Et 3.49 352G OH- Et IIF-534 i- H i-Bu 4-OH-Bnzl 3.12 412 F Pnt IIF-535 Chm H i-Bu2-Cbx-Et 2.84 404 F IIF-536 2- H 1-Npm Ph-Et 3.72 496 F Cbx- Et IIF-5372- H 1-Npm i-Pnt 3.65 462 F Cbx- Et IIF-538 Ph- H 1-Npm 2-Cbx-Et 3.47496 F Et IIF-539 4-F- H 1-Npm 2-Cbx-Et 3.3 500 F Bnzl IIF-540 2- H 1-Npm2-Cbx-Et 2.87 436 F OH- Et IIF-541 i- H 1-Npm 2-Cbx-Et 3.34 462 F PntIIF-542 Chm H 1-Npm 2-Cbx-Et 3.4 488 F IIF-543 4- H i-Pr Ph-Et 3.19 432F OH- Bnzl IIF-544 4- H i-Pr i-Pnt 3.09 398 F OH- Bnzl IIF-545 2- H i-PrPh-Et 2.92 398 F Cbx- Et IIF-546 2- H i-Pr 2-OH-Et 3.02 338 G Cbx- EtIIF-547 Ph- H i-Pr 2-Cbx-Et 2.65 398 F Et IIF-548 Ph- H i-Pr 2-OH-Et2.62 370 F Et IIF-549 4-F- H i-Pr 2-Cbx-Et 2.5 402 F Bnzl IIF-550 4-F- Hi-Pr 2-OH-Et 2.47 374 F Bnzl IIF-551 2- H i-Pr Bnzl 2.69 356 F OH- EtIIF-552 2- H i-Pr i-Bu 2.57 322 F OH- Et IIF-553 2- H i-Pr 1-Npm 3.07406 F OH- Et IIF-554 2- H i-Pr 4-OH-Bnzl 2.45 372 F OH- Et IIF-555 2- Hi-Pr 2-Cbx-Et 3.12 338 G OH- Et IIF-556 2- H i-Pr Ph-Et 2.9 370 F OH- EtIIF-557 2- H i-Pr i-Pnt 2.82 336 F OH- Et IIF-558 i- H i-Pr 4-OH-Bnzl2.88 398 F Pnt IIF-559 i- H i-Pr 2-Cbx-Et 2.49 364 F Pnt IIF-560 i- Hi-Pr 2-OH-Et 3.67 336 G Pnt IIF-561 i-Bu H s-Bu 2-OH-Et 3.69 336 GIIF-562 4- H s-Bu Ph-Et 3.35 446 F OH- Bnzl IIF-563 4- H s-Bu i-Pnt 3.2412 F OH- Bnzl IIF-564 2- H s-Bu i-Pnt 3.09 378 F Cbx- Et IIF-565 Ph- Hs-Bu 2-Cbx-Et 2.8 412 F Et IIF-566 4-F- H s-Bu 2-Cbx-Et 2.69 416 F BnzlIIF-567 2- H s-Bu 4-OH-Bnzl 2.67 386 F OH- Et IIF-568 2- H s-Bu 2-Cbx-Et3.47 352 G OH- Et IIF-569 i- H s-Bu 4-OH-Bnzl 3.07 412 F Pnt IIF-570 i Hs-Bu 2-Cbx-Et 2.67 378 F Pnt IIF-571 Chm H s-Bu 4-OH-Bnzl 3.2 438 FIIF-572 Chm H s-Bu 2-Cbx-Et 2.8 404 F IIF-573 i-Bu H 4-OH- i-Pnt 3.1 412F Bnzl IIF-574 2- H 4-OH- Ph-Et 2.77 462 F Cbx- Bnzl Et IIF-575 2- H4-OH- i-Pnt 2.72 428 F Cbx- Bnzl Et IIF-576 Ph- H 4-OH- 2-Cbx-Et 2.67462 F Et Bnzl IIF-577 4-F- H 4-OH- 2-Cbx-Et 2.55 466 F Bnzl Bnzl IIF-5782- H 4-OH- 2-Cbx-Et 3.2 402 G OH- Bnzl Et IIF-579 i- H 4-OH- 2-Cbx-Et2.52 428 F Pnt Bnzl IIF-580 Chm H 4-OH- 2-Cbx-Et 2.67 454 F Bnzl IIF-581i-Bu H 2-Cbx-Et Ph-Et 2.82 412 F IIF-582 i-Bu H 2-Cbx-Et i-Pnt 2.72 378F IIF-583 i- H 2-Cbx-Et i-Bu 2.74 378 F Pnt IIF-584 i- H 2-Cbx-Et4-OH-Bnzl 2.45 428 F Pnt IIF-585 Chm H 2-Cbx-Et i-Bu 2.94 404 F IIF-586Chm H 2-Cbx-Et i-Pnt 3.17 418 F IIF-587 Bnzl H 4-F-Bnzl 4-OH-Bnzl 3.25484 F IIF-588 Bnzl H 4-F-Bnzl 2-Cbx-Et 2.88 450 F IIF-589 i-Bu H4-F-Bnzl 4-OH-Bnzl 3.12 450 F IIF-590 i-Bu H 4-F-Bnzl 2-Cbx-Et 2.72 416F IIF-591 1- H 4-F-Bnzl 4-OH-Bnzl 3.5 534 F Npm IIF-592 1- H 4-F-Bnzl2-Cbx-Et 3.13 500 F Npm IIF-593 4- H 4-F-Bnzl 2-Cbx-Et 2.7 466 F OH-Bnzl IIF-594 4- H 4-F-Bnzl Ph-Et 3.5 498 F OH- Bnzl IIF-595 4- H4-F-Bnzl i-Pnt 3.44 464 F OH- Bnzl IIF-596 2- H 4-F-Bnzl 4-OH-Bnzl 2.9466 F Cbx- Et IIF-597 2- H 4-F-Bnzl Ph-Et 3.32 464 F Cbx- Et IIF-598 2-H 4-F-Bnzl i-Pnt 3.25 430 F Cbx- Et IIF-599 Ph- H 4-F-Bnzl 4-OH-Bnzl3.42 498 F Et IIF-600 Ph- H 4-F-Bnzl 2-Cbx-Et 3.07 464 F Et IIF-601 2- H4-F-Bnzl 4-OH-Bnzl 2.84 438 F OH- Et IIF-602 2- H 4-F-Bnzl 2-Cbx-Et 2.52404 F OH- Et IIF-603 i- H 4-F-Bnzl 4-OH-Bnzl 3.27 464 F Pnt IIF-604 ChmH 4-F-Bnzl 4-OH-Bnzl 3.37 490 F IIF-605 Chm H 4-F-Bnzl 2-Cbx-Et 3 456 FIIF-606 i-Bu H i-Pnt 2-Cbx-Et 2.72 378 F IIF-607 4- H i-Pnt 2-Cbx-Et2.72 428 F OH- Bnzl IIF-608 2- H i-Pnt i-Bu 3.1 378 F Cbx- Et IIF-609 2-H i-Pnt 4-OH-Bnzl 2.94 428 F Cbx- Et IIF-610 2- H i-Pnt i-Bu 3.04 350 FOH- Et IIF-611 Chm H i-Pnt 2-Cbx-Et 3.05 418 F IIF-612 i-Bu H 2-OH-Eti-Bu 2.43 336 F IIF-613 i-Bu H 2-OH-Et 4-OH-Bnzl 1.34 386 F IIF-614 i-BuH 2-OH-Et 2-Cbx-Et 2.57 352 F IIF-615 1- H 2-OH-Et 4-OH-Bnzl 2.62 470 FNpm IIF-616 1- H 2-OH-Et 2-Cbx-Et 2.45 436 F Npm IIF-617 4- H 2-OH-EtBnzl 2.43 420 F OH- Bnzl IIF-618 4- H 2-OH-Et 1-Npm 2.74 470 F OH- BnzlIIF-619 4- H 2-OH-Et i-Pnt 2.45 400 F OH- Bnzl IIF-620 2- H 2-OH-Et Bnzl3.32 386 F Cbx- Et IIF-621 2- H 2-OH-Et 4-OH-Bnzl 2.94 402 G Cbx- EtIIF-622 2- H 2-OH-Et i-Pnt 3.42 366 G Cbx- Et IIF-623 Bnzl H Ph-Et4-OH-Bnzl 3.29 480 F IIF-624 Bnzl H Ph-Et 2-Cbx-Et 2.9 446 F IIF-625i-Bu H Ph-Et 4-OH-Bnzl 3.15 446 F IIF-626 i-Bu H Ph-Et 2-Cbx-Et 2.77 412F IIF-627 1- H Ph-Et 4-OH-Bnzl 3.55 530 F Npm IIF-628 4- H Ph-Et i-Pnt3.57 460 F OH- Bnzl IIF-629 2- H Ph-Et 4-OH-Bnzl 2.95 462 F Cbx- EtIIF-630 4-F- H Ph-Et 4-OH-Bnzl 3.3 498 F Bnzl IIF-631 2- H Ph-Et4-OH-Bnzl 2.88 434 F OH- Et IIF-632 i- H Ph-Et 4-OH-Bnzl 3.37 460 F PntIIF-633 i- H Ph-Et 2-Cbx-Et 2.99 426 F Pnt IIF-634 Chm H Ph-Et 4-OH-Bnzl3.47 486 F IIF-635 Chm H Ph-Et 2-Cbx-Et 3.1 452 F IIF-636 Bnzl H Hxy2-Cbx-Et 3.15 426 F IIF-637 4- H Hxy 1-Npm 4.15 510 F OH- Bnzl IIF-6384- H Hxy 2-Cbx-Et 3 442 F OH- Bnzl IIF-639 2- H Hxy i-Bu 3.4 392 F Cbx-Et IIF-640 2- H Hxy 1-Npm 3.85 476 F Cbx- Et IIF-641 2- H Hxy 4-OH-Bnzl3.22 442 F Cbx- Et IIF-642 2- H Hxy i-Pnt 3.65 406 F Cbx- Et IIF-643 Ph-H Hxy 2-Cbx-Et 3.37 440 F Et IIF-644 4-F- H Hxy 2-Cbx-Et 3.2 444 F BnzlIIF-645 2- H Hxy i-Bu 3.35 364 F OH- Et IIF-646 2- H Hxy 4-OH-Bnzl 3.15414 F OH- Et IIF-647 2- H Hxy 2-Cbx-Et 2.79 380 F OH- Et IIF-648 2- HHxy i-Pnt 3.55 378 F OH- Et IIF-649 i- H Hxy 4-OH-Bnzl 3.69 440 F PntIIF-650 i- H Hxy 2-Cbx-Et 3.24 406 F Pnt IIF-651 i- H Hxy 2-OH-Et 3.24378 F Pnt IIF-652 Chm H Hxy 4-OH-Bnzl 3.75 466 F IIF-653 Chm H Hxy2-Cbx-Et 3.35 432 F IIF-654 tBOC- H Bnzl i-Pnt 4.09 468 F E IIF-655Ph-Et H Bnzl tBOC-E 4.04 502 F IIF-656 4-F- H Bnzl tBOC-E 3.8 506 F BnzlIIF-657 tBOC- H i-Bu Ph-Et 3.92 468 F E IIF-658 4-F- H i-Bu tBOC-E 3.7472 F Bnzl IIF-659 i-Pnt H i-Bu 4-tBuO-Bnzl 4.39 468 F IIF-660 Chm Hi-Bu 4-tBuO-Bnzl 4.35 494 F IIF-661 Chm H i-Bu tBOC-E 3.94 460 F IIF-662tBOC- H 1-Npm Ph-Et 4.47 552 F E IIF-663 tBOC- H 1-Npm i-Pnt 4.52 518 FE IIF-664 Ph-Et H 1-Npm tBOC-E 4.39 552 F IIF-665 4-F- H 1-Npm tBOC-E4.25 556 F Bnzl IIF-666 2- H 1-Npm tBOC-E 4.89 548 F OtBu- Et IIF-667i-Pnt H 1-Npm tBOC-E 4.35 518 F IIF-668 Chm H 1-Npm tBOC-E 4.54 544 FIIF-669 4- H i-Pr i-Pnt 4.07 454 F tBuO- Bnzl IIF-670 tBOC- H i-Pr Ph-Et3.72 454 F E IIF-671 2- H i-Pr 1-Npm 3.87 462 F OtBu- Et IIF-672 2- Hi-Pr 4-tBuO-Bnzl 3.9 484 F OtBu- Et IIF-673 Chm H i-Pr 4-tBuO-Bnzl 4.07480 F IIF-674 4- H s-Bu Ph-Et 4.22 502 F tBuO- Bnzl IIF-675 4- H s-Bui-Pnt 4.07 468 F tBuO- Bnzl IIF-676 tBOC- H s-Bu i-Pnt 3.82 434 F EIIF-677 Ph-Et H s-Bu tBOC-E 3.84 468 F IIF-678 4-F- H s-Bu tBOC-E 3.95472 F Bnzl IIF-679 2- H s-Bu tBOC-E 3.7 464 F OtBu- Et IIF-680 i-Pnt Hs-Bu 4-tBuO-Bnzl 4.12 468 F IIF-681 i-Pnt H s-Bu tBOC-E 3.7 434 FIIF-682 Chm H s-Bu 4-tBuO-Bnzl 4.35 494 F IIF-683 i-Bu H 4-tBuO- i-Pnt4.07 468 F Bnzl IIF-684 tBOC- H 4-tBuO- Ph-Et 4.52 574 F E Bnzl IIF-685tBOC- H 4-tBuO- i-Pnt 4.42 540 F E Bnzl IIF-686 Ph-Et H 4-tBuO- tBOC-E4.52 574 F Bnzl IIF-687 4-F- H 4-tBuO- tBOC-E 4.22 578 F Bnzl BnzlIIF-688 Chm H 4-tBuO- tBOC-E 4.54 566 F Bnzl IIF-689 i-Bu H tBOC-E i-Pnt3.7 434 F IIF-690 Bnzl H 4-F-Bnzl 4-tBuO-Bnzl 4.17 540 F IIF-691 i-Bu H4-F-Bnzl 4-tBuO-Bnzl 3.99 506 F IIF-692 i-Bu H 4-F-Bnzl tBOC-E 3.67 472F IIF-693 1-Npm H 4-F-Bnzl 4-tBuO-Bnzl 4.59 590 F IIF-694 1-Npm H4-F-Bnzl tBOC-E 4.17 556 F IIF-695 4- H 4-F-Bnzl tBOC-E 4.34 578 F tBuO-Bnzl IIF-696 4- H 4-F-Bnzl Ph-Et 4.75 554 F tBuO- Bnzl IIF-697 4- H4-F-Bnzl i-Pnt 4.42 520 F tBuO- Bnzl IIF-698 tBOC- H 4-F-Bnzl4-tBuO-Bnzl 4.39 578 F E IIF-699 tBOC- H 4-F-Bnzl i-Pnt 4.09 486 F EIIF-700 Ph-Et H 4-F-Bnzl 4-tBuO-Bnzl 4.34 554 F IIF-701 2- H 4-F-Bnzl4-tBuO-Bnzl 4.32 550 F OtBu- Et IIF-702 i-Pnt H 4-F-Bnzl 4-tBuO-Bnzl4.29 520 F IIF-703 Chm H 4-F-Bnzl 4-tBuO-Bnzl 4.39 546 F IIF-704 Chm H4-F-Bnzl tBOC-E 4.05 512 F IIF-705 4- H i-Pnt tBOC-E 4.32 540 F tBuO-Bnzl IIF-706 tBOC- H i-Pnt 4-tBuO-Bnzl 4.54 540 F E IIF-707 i-Bu H2-OtBu- 4-tBuO-Bnzl 3.87 498 F Et IIF-708 1-Npm H 2-OtBu- 4-tBuO-Bnzl4.47 582 F Et IIF-709 1-Npm H 2-OtBu- tBOC-E 4 548 F Et IIF-710 4- H2-OtBu- Bnzl 4.02 532 F tBuO- Et Bnzl IIF-711 4- H 2-OtBu- i-Pnt 4.25512 F tBuO- Et Bnzl IIF-712 tBOC- H 2-OtBu- Bnzl 3.67 498 F E Et IIF-713tBOC- H 2-OtBu- 4-tBuO-Bnzl 4.17 570 F E Et IIF-714 Bnzl H Ph-Et4-tBuO-Bnzl 4.25 536 F IIF-715 i-Bu H Ph-Et 4-tBuO-Bnzl 4.1 502 FIIF-716 1-Npm H Ph-Et 4-tBuO-Bnzl 4.59 586 F IIF-717 1-Npm H Ph-EttBOC-E 4.2 552 F IIF-718 4-F- H Ph-Et 4-tBuO-Bnzl 4.29 554 F BnzlIIF-719 2- H Ph-Et 4-tBuO-Bnzl 4.39 546 F OtBu- Et IIF-720 i-Pnt H Ph-Et4-tBuO-Bnzl 4.37 516 F IIF-721 Chm H Ph-Et 4-tBuO-Bnzl 4.54 542 FIIF-722 Chm H Ph-Et tBOC-E 4.05 508 F IIF-723 4- H Hxy 1-Npm 5.09 566 FtBuO- Bnzl IIF-724 4- H Hxy tBOC-E 4.74 554 F tBuO- Bnzl IIF-725 tBOC- HHxy 4-tBuO-Bnzl 4.8 554 F E IIF-726 Ph-Et H Hxy tBOC-E 4.45 496 FIIF-727 4-F- H Hxy tBOC-E 4.27 500 F Bnzl IIF-728 2- H Hxy 4-tBuO-Bnzl4.79 526 F OtBu- Et IIF-729 2- H Hxy i-Pnt 4.42 434 F OtBu- Et IIF-730i-Pnt H Hxy 4-tBuO-Bnzl 4.74 496 F IIF-731 Chm H Hxy 4-tBuO-Bnzl 4.87522 F IIF-732 i-Bu H i-Bu Ph-Et 3.11 396 H IIF-733 i-Bu H i-Bu i-Pnt2.96 362 H IIF-734 1-Npm H i-Bu i-Pnt 3.25 446 H IIF-735 4-F- H i-Bui-Bu 2.88 400 H Bnzl IIF-736 4-F- H i-Bu 1-Npm 3.12 484 H Bnzl IIF-7374-F- H i-Bu Ph-Et 2.98 448 H Bnzl IIF-738 4-F- H i-Bu i-Pnt 2.98 414 HBnzl IIF-739 i-Pnt H i-Bu i-Bu 2.92 362 H IIF-740 i-Pnt H i-Bu 1-Npm3.17 446 H IIF-741 i-Pnt H i-Bu Ph-Et 2.99 410 H IIF-742 Chm H i-Bu i-Bu2.99 388 H IIF-743 Chm H i-Bu 1-Npm 3.31 472 H IIF-744 Chm H i-Bu Ph-Et3.1 436 H IIF-745 Chm H i-Bu i-Pnt 3.13 402 H IIF-746 Bnzl H Bnzl Ph-Et3.22 464 H IIF-747 1-Npm H Bnzl i-Pnt 3.17 480 H IIF-748 Ph-Et H Bnzl1-Npm 3.27 514 H IIF-749 Ph-Et H Bnzl i-Pnt 3.12 444 H IIF-750 4-F- HBnzl 1-Npm 3.19 518 H Bnzl IIF-751 4-F- H Bnzl Ph-Et 3.02 482 H BnzlIIF-752 4-F- H Bnzl i-Pnt 3.05 448 H Bnzl IIF-753 i- H Bnzl 1-Npm 3.2480 H Pnt IIF-754 Chm H Bnzl 1-Npm 3.3 506 H IIF-755 Chm H Bnzl Ph-Et3.12 470 H IIF-756 Chm H Bnzl i-Pnt 3.15 436 H IIF-757 Bnzl H 1-NpmPh-Et 3.22 514 H IIF-758 Bnzl H 1-Npm i-Pnt 3.27 480 H IIF-759 i-Bu H1-Npm i-Pnt 3.13 446 H IIF-760 1- H 1-Npm Ph-Et 3.34 564 H Npm IIF-7611- H 1-Npm i-Pnt 3.38 530 H Npm IIF-762 Ph- H 1-Npm Bnzl 3.27 514 H EtIIF-763 Ph- H 1-Npm i-Bu 3.22 480 H Et IIF-764 Ph- H 1-Npm 1-Npm 3.42564 H Et IIF-765 Ph- H 1-Npm i-Pnt 3.32 494 H Et IIF-766 4-F- H 1-Npm1-Npm 3.36 568 H Bnzl IIF-767 4-F- H 1-Npm Ph-Et 3.22 532 H Bnzl IIF-7684-F- H 1-Npm i-Pnt 3.24 498 H Bnzl IIF-769 i- H 1-Npm i-Bu 3.22 446 HPnt IIF-770 i- H 1-Npm 1-Npm 3.39 530 H Pnt IIF-771 i- H 1-Npm Ph-Et3.27 494 H Pnt IIF-772 Chm H 1-Npm Bnzl 3.38 506 H IIF-773 Chm H 1-Npmi-Bu 3.3 472 H IIF-774 Chm H 1-Npm 1-Npm 3.49 556 H IIF-775 Chm H 1-NpmPh-Et 3.36 520 H IIF-776 Chm H 1-Npm i-Pnt 3.38 486 H IIF-777 Bnzl Hi-Pr Ph-Et 3 416 H IIF-778 Bnzl H i-Pr i-Pnt 3.01 382 H IIF-779 i-Bu Hi-Pr Ph-Et 2.93 382 H IIF-780 1- H i-Pr Ph-Et 3.14 466 H Npm IIF-781 1-H i-Pr i-Pnt 3.17 432 H Npm IIF-782 Ph- H i-Pr Bnzl 2.99 416 H EtIIF-783 Ph- H i-Pr i-Bu 2.95 382 H Et IIF-784 Ph- H i-Pr 1-Npm 3.22 466H Et IIF-785 Ph- H i-Pr i-Pnt 3.08 396 H Et IIF-786 4-F- H i-Pr Bnzl2.92 420 H Bnzl IIF-787 4-F- H i-Pr i-Bu 2.92 386 H Bnzl IIF-788 4-F- Hi-Pr 1-Npm 3.14 470 H Bnzl IIF-789 4-F- H i-Pr Ph-Et 2.98 434 H BnzlIIF-790 4-F- H i-Pr i-Pnt 2.97 400 H Bnzl IIF-791 i- H i-Pr Bnzl 2.91382 H Pnt IIF-792 i- H i-Pr 1-Npm 3.16 432 H Pnt IIF-793 i- H i-Pr Ph-Et3.02 396 H Pnt IIF-794 Chm H i-Pr Bnzl 3.05 408 H IIF-795 Chm H i-Pr1-Npm 3.28 458 H IIF-796 Chm H i-Pr Ph-Et 3.09 422 H IIF-797 Bnzl H s-BuPh-Et 3.07 430 H IIF-798 Bnzl H s-Bu i-Pnt 3.07 396 H IIF-799 i-Bu Hs-Bu Ph-Et 3 396 H IIF-800 1- H s-Bu Ph-Et 3.21 480 H Npm IIF-801 1- Hs-Bu i-Pnt 3.22 446 H Npm IIF-802 Ph- H s-Bu Bnzl 3.09 430 H Et IIF-803Ph- H s-Bu i-Bu 3.05 396 H Et IIF-804 Ph- H s-Bu 1-Npm 3.28 480 H EtIIF-805 Ph- H s-Bu i-Pnt 3.17 410 H Et IIF-806 4-F- H s-Bu Bnzl 3.07 434H Bnzl IIF-807 4-F- H s-Bu i-Bu 2.97 400 H Bnzl IIF-808 4-F- H s-Bu1-Npm 3.22 484 H Bnzl IIF-809 4-F- H s-Bu Ph-Et 3.06 448 H Bnzl IIF-8104-F- H s-Bu i-Pnt 3.1 414 H Bnzl IIF-811 i- H s-Bu Bnzl 3.05 396 H PntIIF-812 i- H s-Bu 1-Npm 3.25 446 H Pnt IIF-813 Chm H s-Bu Bnzl 3.15 422H IIF-814 Chm H s-Bu 1-Npm 3.34 472 H IIF-815 Bnzl H Ph-Et Bnzl 3.07 464H IIF-816 Bnzl H Ph-Et 1-Npm 3.31 514 H IIF-817 Bnzl H Ph-Et i-Pnt 3.15444 H IIF-818 i-Bu H Ph-Et i-Bu 2.96 396 H IIF-819 i-Bu H Ph-Et 1-Npm3.22 480 H IIF-820 i-Bu H Ph-Et i-Pnt 4.26 410 H IIF-821 1- H Ph-Et Bnzl3.29 514 H Npm IIF-822 1- H Ph-Et i-Bu 3.26 480 H Npm IIF-823 1- H Ph-Et1-Npm 3.42 564 H Npm IIF-824 4-F- H Ph-Et Bnzl 3.08 482 H Bnzl IIF-8254-F- H Ph-Et i-Bu 3.04 448 H Bnzl IIF-826 4-F- H Ph-Et 1-Npm 3.24 532 HBnzl IIF-827 4-F- H Ph-Et i-Pnt 3.13 462 H Bnzl IIF-828 i- H Ph-Et i-Bu3.07 410 H Pnt IIF-829 i- H Ph-Et 1-Npm 3.28 494 H Pnt IIF-830 Chm HPh-Et Bnzl 3.19 470 H IIF-831 Chm H Ph-Et i-Bu 3.12 436 H IIF-832 Chm HPh-Et 1-Npm 3.34 520 H IIF-833 Chm H Ph-Et i-Pnt 3.24 450 H IIF-834 BnzlH 4-F-Bnzl Bnzl 3.03 468 H IIF-835 Bnzl H 4-F-Bnzl 1-Npm 3.19 518 HIIF-836 Bnzl H 4-F-Bnzl Ph-Et 3.06 482 H IIF-837 Bnzl H 4-F-Bnzl i-Pnt3.08 448 H IIF-838 i-Bu H 4-F-Bnzl i-Bu 2.92 400 H IIF-839 i-Bu H4-F-Bnzl 1-Npm 3.16 484 H IIF-840 i-Bu H 4-F-Bnzl i-Pnt 3.03 414 HIIF-841 1- H 4-F-Bnzl Bnzl 3.31 518 H Npm IIF-842 1- H 4-F-Bnzl i-Bu3.23 484 H Npm IIF-843 1- H 4-F-Bnzl 1-Npm 3.47 568 H Npm IIF-844 1- H4-F-Bnzl Ph-Et 3.29 532 H Npm IIF-845 1- H 4-F-Bnzl i-Pnt 3.31 498 H NpmIIF-846 Ph- H 4-F-Bnzl Bnzl 3.16 482 H Et IIF-847 Ph- H 4-F-Bnzl i-Bu3.11 448 H Et IIF-848 Ph- H 4-F-Bnzl 1-Npm 3.31 532 H Et IIF-849 Ph- H4-F-Bnzl i-Pnt 3.2 462 H Et IIF-850 i- H 4-F-Bnzl Bnzl 3.05 448 H PntIIF-851 i- H 4-F-Bnzl 1-Npm 3.21 498 H Pnt IIF-852 i- H 4-F-Bnzl Ph-Et3.13 462 H Pnt IIF-853 Chm H 4-F-Bnzl Bnzl 3.12 474 H IIF-854 Chm H4-F-Bnzl i-Bu 3.09 440 H IIF-855 Chm H 4-F-Bnzl 1-Npm 3.3 524 H IIF-856Chm H 4-F-Bnzl Ph-Et 3.21 488 H IIF-857 Chm H 4-F-Bnzl i-Pnt 3.17 454 HIIF-858 Bnzl H i-Pnt Bnzl 3.08 430 H IIF-859 Bnzl H i-Pnt 1-Npm 3.28 480H IIF-860 Bnzl H i-Pnt Ph-Et 3.12 444 H IIF-861 i-Bu H i-Pnt 1-Npm 3.23446 H IIF-862 i-Bu H i-Pnt Ph-Et 3.11 410 H IIF-863 1-Npm H i-Pnt Bnzl3.25 480 H IIF-864 1-Npm H i-Pnt i-Bu 3.22 446 H IIF-865 1-Npm H i-Pnt1-Npm 3.42 530 H IIF-866 Ph-Et H i-Pnt Bnzl 3.16 444 H IIF-867 Ph-Et Hi-Pnt i-Bu 3.13 410 H IIF-868 Ph-Et H i-Pnt 1-Npm 3.33 494 H IIF-8694-F- H i-Pnt Bnzl 3.09 448 H Bnzl IIF-870 4-F- H i-Pnt i-Bu 3.05 414 HBnzl IIF-871 4-F- H i-Pnt 1-Npm 3.29 498 H Bnzl IIF-872 4-F- H i-PntPh-Et 3.13 462 H Bnzl IIF-873 Chm H i-Pnt Bnzl 3.23 436 H IIF-874 Chm Hi-Pnt 1-Npm 3.42 486 H IIF-875 Chm H i-Pnt Ph-Et 3.25 450 H IIF-876 BnzlH Hxy Bnzl 3.24 444 H IIF-877 Bnzl H Hxy 1-Npm 3.39 494 H IIF-878 Bnzl HHxy i-Pnt 3.27 424 H IIF-879 i-Bu H Hxy 1-Npm 3.36 460 H IIF-880 1-Npm HHxy 1-Npm 3.54 544 H IIF-881 1-Npm H Hxy i-Pnt 3.43 474 H IIF-882 Ph-EtH Hxy Bnzl 3.3 458 H IIF-883 Ph-Et H Hxy i-Bu 3.24 424 H IIF-884 Ph-Et HHxy i-Pnt 3.35 438 H IIF-885 4-F- H Hxy Bnzl 3.23 462 H Bnzl IIF-8864-F- H Hxy i-Bu 3.17 428 H Bnzl IIF-887 4-F- H Hxy 1-Npm 3.4 512 H BnzlIIF-888 4-F- H Hxy Ph-Et 3.24 476 H Bnzl IIF-889 4-F- H Hxy i-Pnt 3.28442 H Bnzl IIF-890 i-Pnt H Hxy Bnzl 3.26 424 H IIF-891 i-Pnt H Hxy 1-Npm3.47 474 H IIF-892 Chm H Hxy Bnzl 3.34 450 H IIF-893 Chm H Hxy 1-Npm 3.5500 H IIF-894 2- H i-Bu Bnzl 4.15 426 H OtBu- Et IIF-895 2- H i-Bu i-Bu4.18 392 H OtBu- Et IIF-896 2- H i-Bu 1-Npm 4.31 476 H OtBu- Et IIF-8972- H i-Bu 4-tBuO-Bnzl 4.37 498 H OtBu- Et IIF-898 2- H i-Bu Ph-Et 4.18440 H OtBu- Et IIF-899 2- H i-Bu i-Pnt 4.28 406 H OtBu- Et IIF-900 2- HBnzl Bnzl 4.2 460 H OtBu- Et IIF-901 2- H Bnzl i-Bu 4.17 426 H OtBu- EtIIF-902 2- H Bnzl 4-tBuO-Bnzl 4.32 532 H OtBu- Et IIF-903 2- H BnzlPh-Et 4.29 474 H OtBu- Et IIF-904 2- H Bnzl i-Pnt 4.27 440 H OtBu- EtIIF-905 i-Pnt H Bnzl 4-tBuO-Bnzl 3.26 502 H IIF-906 Chm H Bnzl4-tBuO-Bnzl 3.32 528 H IIF-907 4- H 1-Npm Ph-Et 3.42 586 H tBuO- BnzlIIF-908 4- H 1-Npm i-Pnt 3.42 552 H tBuO- Bnzl IIF-909 Ph-Et H 1-Npm4-tBuO-Bnzl 3.4 586 H IIF-910 4-F- H 1-Npm 4-tBuO-Bnzl 3.4 590 H BnzlIIF-911 2- H 1-Npm Bnzl 4.38 510 H OtBu- Et IIF-912 2- H 1-Npm i-Bu 4.35476 H OtBu- Et IIF-913 2- H 1-Npm 1-Npm 4.5 560 H OtBu- Et IIF-914 i-PntH 1-Npm 4-tBuO-Bnzl 3.43 552 H IIF-915 Chm H 1-Npm 4-tBuO-Bnzl 3.5 578 HIIF-916 Bnzl H 4-tBuO- Ph-Et 3.31 536 H Bnzl IIF-917 Bnzl H 4-tBuO-i-Pnt 3.29 502 H Bnzl IIF-918 i-Bu H 4-tBuO- Ph-Et 3.22 502 H BnzlIIF-919 1-Npm H 4-tBuO- Ph-Et 3.41 586 H Bnzl IIF-920 1-Npm H 4-tBuO-i-Pnt 3.41 552 H Bnzl IIF-921 Ph-Et H 4-tBuO- Bnzl 3.32 536 H BnzlIIF-922 Ph-Et H 4-tBuO- 1-Npm 3.43 586 H Bnzl IIF-923 Ph-Et H 4-tBuO-i-Pnt 3.37 516 H Bnzl IIF-924 4-F- H 4-tBuO- Bnzl 3.22 540 H Bnzl BnzlIIF-925 4-F- H 4-tBuO- 1-Npm 3.38 590 H Bnzl Bnzl IIF-926 4-F- H 4-tBuO-Ph-Et 3.28 554 H Bnzl Bnzl IIF-927 4-F- H 4-tBuO- i-Pnt 3.29 520 H BnzlBnzl IIF-928 2- H 4-tBuO- 1-Npm 3.46 582 H OtBu- Bnzl Et IIF-929 i-Pnt H4-tBuO- i-Bu 3.2 468 H Bnzl IIF-930 i-Pnt H 4-tBuO- 1-Npm 3.42 552 HBnzl IIF-931 i-Pnt H 4-tBuO- Ph-Et 3.33 516 H Bnzl IIF-932 Chm H 4-tBuO-Bnzl 3.33 528 H Bnzl IIF-933 Chm H 4-tBuO- i-Bu 3.24 494 H Bnzl IIF-934Chm H 4-tBuO- 1-Npm 3.5 578 H Bnzl IIF-935 Chm H 4-tBuO- Ph-Et 3.41 542H Bnzl IIF-936 Chm H 4-tBuO- i-Pnt 3.42 508 H Bnzl IIF-937 Bnzl H tBOC-EPh-Et 3.08 502 H IIF-938 Bnzl H tBOC-E i-Pnt 3.08 468 H IIF-939 1-Npm HtBOC-E Ph-Et 3.25 552 H IIF-940 1-Npm H tBOC-E i-Pnt 3.26 518 H IIF-9414- H tBOC-E Ph-Et 3.32 574 H tBuO- Bnzl IIF-942 4- H tBOC-E i-Pnt 3.34540 H tBuO- Bnzl IIF-943 Ph-Et H tBOC-E Bnzl 3.08 502 H IIF-944 Ph-Et HtBOC-E i-Bu 3.12 468 H IIF-945 Ph-Et H tBOC-E 1-Npm 3.27 552 H IIF-946Ph-Et H tBOC-E 4-tBuO-Bnzl 3.33 574 H IIF-947 Ph-Et H tBOC-E i-Pnt 3.18482 H IIF-948 4-F- H tBOC-E Bnzl 3.06 506 H Bnzl IIF-949 4-F- H tBOC-Ei-Bu 3.04 472 H Bnzl IIF-950 4-F- H tBOC-E 1-Npm 3.23 556 H Bnzl IIF-9514-F- H tBOC-E 4-tBuO-Bnzl 3.27 578 H Bnzl IIF-952 4-F- H tBOC-E Ph-Et3.12 520 H Bnzl IIF-953 4-F- H tBOC-E i-Pnt 3.13 486 H Bnzl IIF-954 2- HtBOC-E Bnzl 3.11 498 H OtBu- Et IIF-955 2- H tBOC-E 1-Npm 3.27 548 HOtBu- Et IIF-956 2- H tBOC-E 4-tBuO-Bnzl 3.37 570 H OtBu- Et IIF-957 2-H tBOC-E Ph-Et 3.17 512 H OtBu- Et IIF-958 i-Pnt H tBOC-E Bnzl 3.08 468H IIF-959 i-Pnt H tBOC-E 1-Npm 3.22 518 H IIF-960 i-Pnt H tBOC-E Ph-Et3.13 482 H IIF-961 Chm H tBOC-E Bnzl 3.17 494 H IIF-962 Chm H tBOC-E1-Npm 3.34 544 H IIF-963 Ph-Et H i-Pr 4-tBuO-Bnzl 3.22 488 H IIF-9644-F- H i-Pr 4-tBuO-Bnzl 3.16 492 H Bnzl IIF-965 Ph-Et H s-Bu 4-tBuO-Bnzl3.29 502 H IIF-966 4-F- H s-Bu 4-tBuO-Bnzl 3.29 506 H Bnzl IIF-967 2- Hs-Bu Bnzl 3.04 426 H OtBu- Et IIF-968 2- H s-Bu i-Bu 3.03 392 H OtBu- EtIIF-969 2- H s-Bu 1-Npm 3.3 476 H OtBu- Et IIF-970 2- H s-Bu Ph-Et 3.15440 H OtBu- Et IIF-971 4- H Ph-Et Bnzl 3.33 536 H tBuO- Bnzl IIF-972 4-H Ph-Et i-Bu 3.25 502 H tBuO- Bnzl IIF-973 4- H Ph-Et 1-Npm 3.47 586 HtBuO- Bnzl IIF-974 tBOC- H Ph-Et Bnzl 3.16 502 H E IIF-975 tBOC- H Ph-Eti-Bu 3.13 468 H E IIF-976 tBOC- H Ph-Et 1-Npm 3.35 552 H E IIF-977 2- HPh-Et Bnzl 3.1 474 H OtBu- Et IIF-978 2- H Ph-Et i-Bu 3.08 440 H OtBu-Et IIF-979 2- H Ph-Et i-Pnt 3.17 454 H OtBu- Et IIF-980 4- H 4-F-BnzlBnzl 3.35 540 H tBuO- Bnzl IIF-981 4- H 4-F-Bnzl i-Bu 3.28 506 H tBuO-Bnzl IIF-982 4- H 4-F-Bnzl 1-Npm 3.47 590 H tBuO- Bnzl IIF-983 tBOC- H4-F-Bnzl Bnzl 3.14 506 H E IIF-984 tBOC- H 4-F-Bnzl i-Bu 3.11 472 H EIIF-985 tBOC- H 4-F-Bnzl 1-Npm 3.32 556 H E IIF-986 2- H 4-F-Bnzl i-Bu3.03 444 H OtBu- Et IIF-987 2- H 4-F-Bnzl Ph-Et 3.13 492 H OtBu- EtIIF-988 2- H 4-F-Bnzl i-Pnt 3.13 458 H OtBu- Et IIF-989 Bnzl H 2-OtBu-Bnzl 4.08 460 H Et IIF-990 Bnzl H 2-OtBu- i-Bu 4.07 426 H Et IIF-991Bnzl H 2-OtBu- 1-Npm 4.26 510 H Et IIF-992 Bnzl H 2-OtBu- Ph-Et 4.17 474H Et IIF-993 Bnzl H 2-OtBu- i-Pnt 4.15 440 H Et IIF-994 i-Bu H 2-OtBu-Bnzl 4.12 426 H Et IIF-995 i-Bu H 2-OtBu- 1-Npm 4.29 476 H Et IIF-996i-Bu H 2-OtBu- Ph-Et 4.16 440 H Et IIF-997 1-Npm H 2-OtBu- i-Bu 4.22 476H Et IIF-998 1-Npm H 2-OtBu- i-Pnt 4.33 490 H Et IIF-999 4- H 2-OtBu-i-Bu 4.3 498 H tBuO- Et Bnzl IIF-1000 Ph-Et H 2-OtBu- Bnzl 4.2 474 H EtIIF-1001 Ph-Et H 2-OtBu- i-Bu 4.17 440 H Et IIF-1002 Ph-Et H 2-OtBu-1-Npm 4.35 524 H Et IIF-1003 Ph-Et H 2-OtBu- 4-tBuO-Bnzl 4.36 546 H EtIIF-1004 Ph-Et H 2-OtBu- i-Pnt 4.28 454 H Et IIF-1005 4-F- H 2-OtBu-Bnzl 4.17 478 H Bnzl Et IIF-1006 4-F- H 2-OtBu- i-Bu 4.05 444 H Bnzl EtIIF-1007 4-F- H 2-OtBu- 1-Npm 4.3 528 H Bnzl Et IIF-1008 4-F- H 2-OtBu-4-tBuO-Bnzl 4.35 550 H Bnzl Et IIF-1009 4-F- H 2-OtBu- Ph-Et 4.18 492 HBnzl Et IIF-1010 4-F- H 2-OtBu- i-Pnt 4.18 458 H Bnzl Et IIF-1011 i-PntH 2-OtBu- Bnzl 4.15 440 H Et IIF-1012 i-Pnt H 2-OtBu- 1-Npm 4.32 490 HEt IIF-1013 i-Pnt H 2-OtBu- 4-tBuO-Bnzl 4.36 512 H Et IIF-1014 i-Pnt H2-OtBu- Ph-Et 4.26 454 H Et IIF-1015 Chm H 2-OtBu- Bnzl 4.25 466 H EtIIF-1016 Chm H 2-OtBu- 4-tBuO-Bnzl 4.41 538 H Et IIF-1017 Chm H 2-OtBu-Ph-Et 4.28 480 H Et IIF-1018 Bnzl H i-Pnt 4-tBuO-Bnzl 3.27 502 HIIF-1019 Bnzl H i-Pnt tBOC-E 3.08 468 H IIF-1020 1-Npm H i-Pnt4-tBuO-Bnzl 3.46 552 H IIF-1021 1-Npm H i-Pnt tBOC-E 3.25 518 H IIF-10224- H i-Pnt Bnzl 3.32 502 H tBuO- Bnzl IIF-1023 4- H i-Pnt i-Bu 3.3 468 HtBuO- Bnzl IIF-1024 4- H i-Pnt 1-Npm 3.53 552 H tBuO- Bnzl IIF-1025 4- Hi-Pnt Ph-Et 3.37 516 H tBuO- Bnzl IIF-1026 tBOC- H i-Pnt Bnzl 3.18 468 HE IIF-1027 tBOC- H i-Pnt 1-Npm 3.38 518 H E IIF-1028 tBOC- H i-Pnt Ph-Et3.22 482 H E IIF-1029 Ph-Et H i-Pnt 4-tBuO-Bnzl 3.39 516 H IIF-1030Ph-Et H i-Pnt tBOC-E 3.22 482 H IIF-1031 4-F- H i-Pnt 4-tBuO-Bnzl 3.29520 H Bnzl IIF-1032 4-F- H i-Pnt tBOC-E 2.35 486 H Bnzl IIF-1033 Chm Hi-Pnt 4-tBuO-Bnzl 2.62 508 H IIF-1034 Bnzl H Hxy 4-tBuO-Bnzl 2.63 516 HIIF-1035 i-Bu H Hxy 4-tBuO-Bnzl 2.55 482 H IIF-1036 1-Npm H Hxy4-tBuO-Bnzl 2.88 566 H IIF-1037 4- H Hxy Bnzl 2.63 516 H tBuO- BnzlIIF-1038 4- H Hxy i-Bu 2.6 482 H tBuO- Bnzl IIF-1039 4- H Hxy Ph-Et 2.67530 H tBuO- Bnzl IIF-1040 4- H Hxy i-Pnt 2.7 496 H tBuO- Bnzl IIF-1041tBOC- H Hxy Ph-Et 2.55 496 H E IIF-1042 Ph-Et H Hxy 4-tBuO-Bnzl 2.68 530H IIF-1043 4-F- H Hxy 4-tBuO-Bnzl 2.63 534 H Bnzl IIF-1044 2- H Hxy Bnzl2.47 454 H OtBu- Et IIF-1045 2- H Hxy 1-Npm 2.63 504 H OtBu- Et IIF-10462- H Hxy Ph-Et 2.5 468 H OtBu- Et IIF-1047 1-Npm H 4-F-Bnzl 2-OTBS-Et1.11 586.4 C ^(†) Ring formed together by R_(2A) and R_(2B) Com- LCMSpound t_(R) Mass Measurement Yield number Name of compound (min) (M +H)⁺ condition (%) IIF-1 (3S*,3aR*,6S*,7R*,7aR*)-N,7- 1.14 416 B  10dibenzyl-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-2(3S*,3aR*,6S*,7R*,7aR*)-N,1,7- 1.11 348 B  16 triisobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-3(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 1.14 382 B  14N,1-diisobutyl-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-4(3S*,3aR*,6S*,7R*,7aR*)-1-benzyl- 1.14 382 B   8N,7-diisobutyl-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-5(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 1.13 382 B  131,7-diisobutyl-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-6(3S*,3aR*,6S*,7R*,7aR*)-1,7- 1.15 416 B  19 dibenzyl-N-isobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6-carboxamide IIF-7 (3S*,3aR*,6S*,7R*,7aR*)-N,1- 1.00 416 B  22dibenzyl-7-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-8(3S*,3aR*,6S*,7R*,7aR*)-N,1,7- 1.16 450 B  21 tribenzyl-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-9(3S*,3aR*,6S*,7R*,7aR*)-N,7- 1.18 430 B  20 dibenzyl-1-isopentyl-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6-carboxamide IIF-10 (3S*,3aR*,6S*,7R*,7aR*)-N,1- 1.18 430 B  11dibenzyl-7-isopentyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-11(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 1.16 430 B  12 1-isobutyl-7-phenethyl-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6-carboxamide IIF-12 (3S*,3aR*,6S*,7R*,7aR*)-1-benzyl- 1.16 430 B  127-isobutyl-N-phenethyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-13(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 1.17 430 B  171-isobutyl-7-(3-methylbenzyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-14(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 1.16 430 B  151-isobutyl-7-(4-methylbenzyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-15(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 1.18 430 B  161-isobutyl-N-(3-methylbenzyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-16(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 1.18 430 B  151-isobutyl-N-(4-methylbenzyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-17(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 1.18 450 B  14N-(3-chlorobenzyl)-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-18(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 1.17 450 B  13N-(4-chlorobenzyl)-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-19(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 1.28 484 B  221-(3,4-dichlorobenzyl)-7- isobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamide IIF-20(3S*,3aR*,6S*,7R*,7aR*)-1-benzyl- 1.25 484 B  21N-(3,4-dichlorobenzyl)-7- isobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamide IIF-23(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.99 488 A  33 1-isobutyl-N-(4-(tert-butoxy)benzyl)-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-24(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.98 466 A  141-isobutyl-N-(naphthalen-1- ylmethyl)-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-25(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.74 370 A   5N-(2-hydroxyethyl)-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-263-((3S*,3aR*,6S*,7R*,7aR*)-7- 0.75 398 A 100benzyl-1-isobutyl-1,2,3,3a,7,7a- hexahydro-1H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide)propanoic acid IIF-27(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.92 454 A  201-isobutyl-N-(2-(tert-butoxy)-2- oxoethyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-28(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.72 397 A  88N-(3-amino-3-oxopropyl)-1- isobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamide IIF-29(3S*,3aR*,6S*,7R*,7aR*)-N-(4- 0.67 397 A 100aminobutyl)-7-benzyl-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-30(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.91 497 A  10 1-isobutyl-N-(4-((tert-butoxycarbonyl)amino)butyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-31(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.98 422 A  12N-cyclohexylmethyl-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-32(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 0.87 424 A  241-isobutyl-N-((tetrahydro-2H- pyran-2-yl)methyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-34(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 0.93 497 A  17 1-isobutyl-7-(4-((tert-butoxycarbonyl)amino)butyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-36(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 0.82 412 A   51-isobutyl-7-(3-methoxy-3- oxopropyl)-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-38(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 0.99 422 A  237-(cyclohexylmethyl)-1-isobutyl- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-39(3S*,3aR*,6S*,7R*,7aR*)-N,7- 0.96 456 A  22 dibenzyl-1-cyclohexylmethyl-1,2,3,3a,7,7a-hexahydro-6H-3,6- methanopyrrolo[3,2-c]pyridine-6-carboxamide IIF-40 (3S*,3aR*,6S*,7R*,7aR*)-N,7- 0.86 466 A  76dibenzyl-1-(4-hydroxybenzyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-41(3S*,3aR*,6S*,7R*,7aR*)-N,7- 1.00 522 A  14 dibenzyl-1-(4-(tert-butoxy)benzyl)-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-42(3S*,3aR*,6S*,7R*,7aR*)-N,7- 0.97 500 A   4 dibenzyl-1-(naphthalen-1-ylmethyl)-1,2,3,3a,7,7a- hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-76 tert-butyl 3- 0.70488 B  22 ((3S*,3aR*,6S*,7R*,7aR*)-7-benzyl- 6-(benzylcarbamoyl)-2,3,3a,6,7,7a-hexahydro-1H-3,6- methanopyrrolo[3,2-c]pyridin-1-yl)propanoate IIF-77 (3S*,3aR*,6S*,7R*,7aR*)-N,1- 0.80 466 B  19dibenzy1-7-(4-hydroxybenzyl)- 1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6- carboxamide IIF-80(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl- 1.01 452 A   61-(naphthalen-1-ylmethyl)-7- propyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamide

Synthesis Example: IF-1 Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-1)

Sodium tetrahydroborate (1.86 mg, 0.0490 mmol) was added to a methanol(0.500 mL) solution of(3S*,3aR*,6S*,7R*,7aR*)-N,7-dibenzyl-1-isobutyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IIF-1) (10.2 mg, 0.0245 mmol) and stirred for 1 hour. After evaporatingthe solvent under reduced pressure, 5% sodium bicarbonate solution (1.00mL) was added to the residue, which was extracted with ethyl acetate(3.00 mL). The organic layer was washed with water (1.00 mL), then driedwith anhydrous sodium sulfate and filtered. The solvent was evaporatedunder reduced pressure. The resulting residue was purified withpreparative PLC silica gel 60F254 (layer thickness 0.500 mm) (ethylacetate:methanol=85:15) to obtain the aforementioned compound (6.37 mg,yield: 62%, RT=0.99 miutes (B method), [M+1]⁺=418).

¹H-NMR spectrum (400 MHz, CDCl₃) δ (ppm): 0.52 (3H, d), 0.58(3H, d),0.89-0.97(1H, m), 1.57-1.62 (1H, m), 1.83-1.94 (3H, m), 2.01-2.07 (1H,m), 2.18-2.24 (2H, m), 2.29 (1H, d), 2.40-2.44 (1H, m), 2.71-2.75 (2H,m), 2.86-2.89 (1H, m), 3.10-3.19 (2H, m), 4.39-4.48 (2H, m), 7.24-7.38(11H, m).

¹³C-NMR spectrum (100 MHz, CDCl₃) δ (ppm): 20.20, 26.99, 33.45, 35.79,36.41, 39.83, 42.13, 42.79, 46.40, 56.95, 61.37, 61.78, 61.97, 125.50,126.96, 127.39, 127.73, 128.25, 129.41, 138.20, 139.59, 175.20.

The three-dimensional structure of the molecules was studied by X-raycrystallography. FIG. 1 shows an ORTEP diagram thereof. DaicelCorporation's chiral column, CHIRALPAK IG (5 μm, 4.6×150 mm), mobilephase: methanol:diethylamine (100:0.1) was used to confirm that themolecule was a racemate through analysis. FIG. 2 shows the chromatogramthereof.

Synthesis Example: D3-1 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-1)

Sodium tetrahydroborate (3.83 mg, 0.101 mmol) was added to a methanol(1.00 mL) solution of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyl-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IIB-1) (21.0 mg, 0.0506 mmol) and stirred for 1 hour. After evaporatingthe solvent under reduced pressure, 5% sodium bicarbonate solution (1.00mL) was added to the residue, which was extracted with ethyl acetate(4.00 mL). The organic layer was washed with water (1.00 mL), then driedwith anhydrous sodium sulfate and filtered. The solvent was evaporatedunder reduced pressure. The resulting residue was purified withpreparative PLC silica gel 60F254 (layer thickness 0.500 mm) (ethylacetate:methanol=90:10) to obtain the aforementioned compound (17.0 mg,yield: 81%, RT=1.21 minutes (B method), [M+1]⁺=418).

¹H-NMR spectrum (400 MHz, CDCl₃) δ (ppm): 0.48 (3H, d), 0.57 (3H, d),1.18-1.28 (1H, m), 1.35-1.39 (1H, m), 1.55 (1H, s), 1.83-1.88 (1H, m),2.09-2.14 (3H, m), 2.24-2.28 (1H, m), 2.45 (1H, s), 2.70-2.75 (1H, m),2.78-2.88 (1H, m), 2.97 (1H, s), 3.20-3.27 (1H, m), 3.28-3.31 (1H, m),4.28-4.33 (1H, m), 4.48-4.53 (1H, m), 7.21-7.27 (1H, m), 9.56 (1H, t).

¹³C-NMR spectrum (400 MHz, CDCl₃) δ (ppm): 20.20, 20.37, 25.84, 26.43,38.09, 38.60, 39.25, 42.99, 58.19, 61.48, 62.33, 66.49, 125.58, 126.77,127.49, 127.93, 128.07, 128.70, 138.22, 140.32, 173.83.

Synthesis Example: IB-29 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N-(4-aminobutyl)-7-benzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-29)

Formic acid (500 μL) was added to(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(4-((tert-butoxycarbonyl)amino)butyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-30) (7.70 mg, 0.0154 mmol) and incubated overnight at roomtemperature. The formic acid was evaporated under reduced pressure toobtain a triformic acid salt of the aforementioned compound (7.60 mg,yield: 92%, RT=0.75 minutes (A method), [M+1]⁺=399).

Synthesis Example: IB-40 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-(4-hydroxybenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-40)

Formic acid (250 μL) was added to(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-(4-(tert-butoxy)benzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-41) (7.80 mg, 0.0149 mmol) and incubated for 3 hours at roomtemperature. The formic acid was evaporated under reduced pressure toobtain a diformic acid salt of the aforementioned compound (6.30 mg,yield: 99%, RT=0.89 minutes (A method), [M+1]⁺=468).

Synthesis Example: IB-74 Synthesis of tert-butyl(3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyl-7-(3-methoxy-3-oxopropyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine-4-carboxylate(IB-74)

(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3-methoxy-3-oxopropyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-36) (23.5 mg, 0.0570 mmol) was dissolved in tetrahydrofuran (0.400mL), and a 30% tetrahydrofuran solution (140 μL, 0.140 mmol) ofdi-tert-butyl dicarbonate was added and heated for 2 hours at 50° C. Thesolvent was evaporated under reduced pressure. The resulting residue waspurified by preparative PLC (Merck 1.05744.0001 (layer thickness 0.500mm) (ethyl acetate:methanol=9:1)) to obtain the aforementioned compound(22.0 mg, yield: 75%, RT=0.97 minutes (A method), [M+1]⁺=514).

Synthesis Example: IB-73 Synthesis of tert-butyl(3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyl-7-(2-carboxyethyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine-4-carboxylate(IB-73)

tert-butyl(3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyl-7-(3-methoxy-3-oxopropyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine-4-carboxylate(IB-74) (22.0 mg, 0.0430 mmol) was dissolved in methanol (1.00 mL), andlithium hydroxide monohydrate (18.0 mg, 0.430 mmol) was added andstirred overnight at room temperature. Methanol was evaporated underreduced pressure. 10% citric acid solvent (450 μL) and ethyl acetatewere added thereto. The organic layer was dried with anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure to obtainthe aforementioned compound (21.40 mg, yield: 100%, RT=0.91 minutes (Amethod), [M+1]⁺=500).

Synthesis Example: IB-75 Synthesis of tert-butyl(3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyl-7-(3-amino-3-oxopropyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine-4-carboxylate(IB-75)

tert-butyl(3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyl-7-(2-carboxyethyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine-4-carboxylate(IB-73) (6.9 mg, 0.0130 mmol) was dissolved in tetrahydrofuran (0.200mL), and carbonyldiimidazole (4.2 mg, 0.0260 mmol) was added and stirredovernight at room temperature. Ammonium water (13 M) (20.0 μL, 0.260mmol) was added thereto and stirred for 1 hour. The solvent wasevaporated. The resulting residue was purified by preparative PLC (FujiSilysia Chemical's CHROMATOREX NH-TLC (layer thickness 0.200 mm) (ethylacetate)) to obtain the aforementioned compound (1.70 mg, yield: 26%,RT=0.86 minutes (A method), [M+1]⁺=499).

Synthesis Example: IB-79 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N³a,7-dibenzyl-1-(cyclohexylmethyl)-N⁴-propylhexahydro-1H-3,6-methanopyrrolo[3,2-b]pyridine-3a,4-dicarboxamide(IB-79)

(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-cyclohexylmethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-39) (4.6 mg, 0.0100 mmol) was dissolved in tetrahydrofuran (0.180mL), then triethylamine (1.6 μL, 0.0120 mmol) and propylisocyanate (1.13μL, 0.120 mmol) were added and incubated for 1 hour at room temperature.The reaction mixture was purified with preparative PLC silica gel 60F254(layer thickness 0.250 mm) (ethyl acetate:methanol=5:1) to obtain theaforementioned compound (3.50 mg, yield: 65%, RT=1.05 minutes (Amethod), [M+1]⁺=543).

Synthesis of3-((3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyloctahydro-1H-3,6-methanopyrrolo[3,2-b]pyridin-7-yl)propanoicacid (IB-35)

Trifluoroacetic acid (200 μL) was added to tert-butyl(3S*,3aS*,6R*,7R*,7aS*)-3a-(benzylcarbamoyl)-1-isobutyl-7-(2-carboxyethyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine-4-carboxylate(IB-73) (5.50 mg, 0.0110 mmol) and incubated overnight at roomtemperature. Trifluoroacetic acid was evaporated under reduced pressureto obtain a ditrifluoroacetic acid salt of the aforementioned compound(6.80 mg, yield: 100%, RT=0.83 minutes (A method), [M+1]⁺=400).

Synthesis Example: IF-26 Synthesis of((3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyloctahydro-1H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide)propanoicacid (IF-26)

Formic acid (0.500 mL) was added to(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(2-(tert-butoxy)-2-oxoethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-27) (15.0 mg, 0.0330 mmol) and heated overnight at 45° C. The formicacid was evaporated under reduced pressure to obtain a diformic acidsalt of the aforementioned compound (16.2 mg, yield: 100%, RT=0.66minutes (A method), [M+1]⁺=400).

Synthesis Example: IF-33 Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-7-(4-aminobutyl)-N-benzyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-33)

Trifluoroacetic acid (200 μL) was added to(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(4-((tert-butoxycarbonyl)amino)butyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-34) (7.80 mg, 0.0156 mmol) and incubated overnight at roomtemperature. The trifluoroacetic acid was evaporated under reducedpressure to obtain a tritrifluoroacetic acid salt of the aforementionedcompound (7.80 mg, yield: 100%, RT=0.62 minutes (A method), [M+1]⁺=399).

Synthesis Example: IF-41

Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(4-(tert-butoxy)benzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-41)

9.50 mg of 10% palladium-carbon was added to a methanol (0.500 mL)solution of(3S*,3aR*,6S*,7R*,7aR*)-N,7-dibenzyl-1-(4-(tert-butoxy)benzyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IIF-41) (11 mg, 0.0210 mmol) and stirred for a week under a hydrogengas atmosphere. After filtering out the palladium-carbon, the solutionwas concentrated. The residue was purified with preparative PLC silicagel 60F254 (layer thickness 0.500 mm) (ethyl acetate:methanol=5:1) toobtain the aforementioned compound (5.70 mg, yield: 52%, RT=0.90 minutes(A method), [M+1]⁺=524).

Synthesis Example: IF-40 Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(4-hydroxybenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-40)

Formic acid (250 μL) was added to(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(4-(tert-butoxy)benzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-41) (5.70 mg, 10.9 mmol) and incubated for 3 hours at roomtemperature. The formic acid was evaporated under reduced pressure toobtain a diformic acid salt of the aforementioned compound (3.20 mg,yield: 52%, RT=0.75 minutes (A method), [M+1]⁺=468).

Synthesis Example: IF-71 Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-14sobutyl-4-methyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-71)

A 37% formalin solution (0.06 mL, 0.736 mmol) was added to atetrahydrofuran (2.00 mL) solution of(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-1) (30.8 mg, 0.0736 mmol) and stirred for 15 minutes at roomtemperature. Sodium triacetoxyborohydride (46.8 mg, 0.221 mmol) wasadded to the reaction mixture, and stirred for 1 hour at roomtemperature. An aqueous 5% sodium bicarbonate solution (2.00 mL) wasadded to the reaction mixture, and the organic phase was extracted withethyl acetate (5.00 mL). The organic layer was washed with water (2.00mL), then dried with anhydrous sodium sulfate and filtered. The solventwas evaporated under reduced pressure. The resulting residue waspurified with preparative PLC silica gel 60F254 (layer thickness 0.500mm) (ethyl acetate:methanol=85:15) to obtain the aforementioned compound(12.1 mg, yield: 38%, RT=1.02 minutes (B method), [M+1]⁺=432).

Synthesis Example: IF-43 Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-N,7-dibenzyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-43)

Triethylamine (0.0156 mL, 1.13 mmol) and acetyl chloride (0.00804 mL,1.13 mmol) were added to a tetrahydrofuran (1.80 mL) solution of(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-1) (31.4 mg, 0.0751 mmol), and stirred for 30 minutes while coolingwith ice. A 5% sodium bicarbonate solution (2.00 mL) was added to thereaction mixture, and the organic phase was extracted with ethyl acetate(5.00 mL). The organic layer was washed with water (2.00 mL), then driedwith anhydrous sodium sulfate and filtered. The solvent was evaporatedunder reduced pressure. The resulting residue was purified withpreparative PLC silica gel 60F254 (layer thickness 0.500 mm) (ethylacetate:methanol=85:15) to obtain the aforementioned compound (17.6 mg,yield: 51%, RT=1.08 minutes (B method),[M+1]⁺=460).

Synthesis Example: IB-68 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-4-benzoyl-N,7-dibenzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-68)

Triethylamine (0.0152 mL, 0.110 mmol) and benzoyl chloride (0.0127 mL,1.10 mmol) were added to a tetrahydrofuran (2.00 mL) solution of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-1) (30.6 mg, 0.0733 mmol) and stirred for 30 minutes while coolingwith ice. An aqueous 5% sodium bicarbonate solution (2.00 mL) was addedto the reaction mixture, and an organic phase was extracted with ethylacetate (5.00 mL). The organic layer was washed with water (2.00 mL),then dried with anhydrous sodium sulfate and filtered. The solvent wasevaporated under reduced pressure. The resulting residue was purifiedwith preparative PLC silica gel 60F254 (layer thickness 0.500 mm) (ethylacetate:methanol=95:5) to obtain the aforementioned compound (14.8 mg,yield: 39%, RT=1.23 minutes (B method), [M+1]⁺=522).

Synthesis Example: IB-69 Synthesis of (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-4-ethyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-69)

An acetaldehyde 2% N,N-dimethylformamide solution (0.870 mL, 0.395 mmol)was added to a tetrahydrofuran (2.00 mL) solution of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-1) (33.0 mg, 0.790 mmol) and stirred for 15 minutes at roomtemperature. Sodium triacetoxyborohydride (50.2 mg, 0.273 mmol) wasadded to the reaction mixture, and further stirred for 2 hours at roomtemperature. An aqueous 5% sodium bicarbonate solution (10.0 mL) wasadded to the reaciotn mixture, and an organic phase was extracted withethyl acetate (30.0 mL). The organic layer was washed twice with water(10.0 mL), then dried with anhydrous sodium sulfate and filtered. Thesolvent was evaporated under reduced pressure. The resulting residue waspurified with preparative PLC silica gel 60F254 (layer thickness 0.500mm) (ethyl acetate:methanol=95:5) to obtain the aforementioned compound(9.85 mg, yield: 28%, RT=1.24 minutes (B method), [M+1]⁺=446).

Synthesis Example: IB-70 Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyl-4-(methoxycarbonyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-70)

Triethylamine (0.0157 mL, 0.113 mmol) and chloroformic acid methyl(0.00870 mL, 0.113 mmol) were added to a tetrahydrofuran (2.00 mL)solution of (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide (IB-1) (31.5 mg,0.0754 mmol), and stirred for 30 minutes while cooling with ice. Afterstirring for 30 minutes at room temperature, a 5% sodium bicarbonatesolution (2.00 mL) was added to the reaction mixture, and the organicphase was extracted with ethyl acetate (5.00 mL). The organic layer waswashed with water (2.00 mL), then dried with anhydrous sodium sulfateand filtered. The solvent was evaporated under reduced pressure. Theresulting residue was purified with preparative PLC silica gel 60F254(layer thickness 0.500 mm) (ethyl acetate:methanol=95:5) to obtain theaforementioned compound (31.0 mg, yield: 87%, RT=1.18 minutes (Bmethod), [M+1]⁺=476).

The following compounds were synthesized by the same method as theSynthesis Examples.

Compounds with a guanidinopropyl group in one of the substituents R₁,R₂, and R₃ were synthesized by the following method. Representativeexamples are provided below.

Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-1-(3-guanidinopropyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(IB-164) and(3S*,3aS*,6S*,7R*,7aS*)-1-(3-guanidinopropyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(IF-162) 1. Synthesis of tert-butyl(3S*,3aR*,6S*,7R*,7aS*)-(3-(7-isobutyl-3a-((naphthalen-1-ylmethyl)carbamoyl)-2,3,3a,6,7,7a-hexahydro-1H-3,6-methanopyrrolo[3,2-b]pyridin-yl)propyl)carbamateandtert-butyl(3S*,3aR*,6S*,7R*,7aR*)-(3-(7-isobutyl-6-(naphthalen-1-ylmethyl)carbamoyl)-2,3,3a,6,7,7a-hexahydro-1H-3,6-methanopyrrolo[3,2-c]pyridin-1-yl)propyl)carbamate

N,N-dimethylformamide (1 mL) was added to 4-methylpentanal (60.1 mg, 0.6mmol), tert-butyl(3-(allylamino)propyl)carbamate (128.6 mg, 0.6 mmol),and molecular sieve 4 A (100 mg), and thenN-(naphthalen-1-ylmethyl)-1,2,4-triazine-3-carboxamide (79.3 mg, 0.3mmol) was added. The reaction mixture was heated for 16 hours at 85° C.,and then filtered. The filtrate was purified by preparative HPLC (HighPerformance Liquid Chromatography). A fraction of the substance ofinterest was concentrated to obtain a mixture of the aforementionedcompound.

2. Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-1-(3-aminopropyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide and(3S*,3aR*,6S*,7R*,7aR*)-1-(3-aminopropyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide

Trifluoroacetic acid (0.3 mL) was added to the compound (mixture)obtained in 1. and stirred for 1 hour at room temperature. Thetrifluoroacetic acid was evaporated to obtain a trifluoroacetic acidsalt of the aforementioned compound (mixture).

3. Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-1-(3-(N,N′-di(tert-butoxycarbonyl)guanidino)propyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamideand(3S*,3aR*,6S*,7R*,7aR*)-1-(3-(N,N′-di(tert-butoxycarbonyl)guanidino)propyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide

1,3-di(tert-butoxycarbonyl)-2-(trifluoromethanesulfonyl)guanidine (234.8mg, 0.6 mmol), triethylamine (60.7 mg, 0.6 mmol), and tetrahydrofuran(0.5 mL) were added to the compound (mixture) obtained in 2. and stirredfor 3 hours at room temperature. The solvent was evaporated to obtain amixture comprising the aforementioned compound. The mixture obtained inthis step was used in synthesis of the next step without purification.

4. Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-1-(3-(N,N′-di(tert-butoxycarbonyl)guanidino)propyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamideand(3S*,3aS*,6S*,7R*,7aS*)-1-(3-(N,N′-di(tert-butoxycarbonyl)guanidino)propyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide

The reaction mixture obtained in 3. was dissolved in methanol (1 mL),then sodium borohydride (22.7 mg, 0.6 mmol) was added and stirred for 2hours at room temperature. The reaction mixture was purified bypreparative HPLC. Fractions of substances of interest were concentratedto obtain each of the aforementioned compounds separately.

5. Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-1-(3-guanidinopropyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide

Trifluoroacetic acid (0.3 mL) was added to(3S*,3aS*,6S*,7R*,7aS*)-1-(3-(N,N′-di(tert-butoxycarbonyl)guanidino)propyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamideobtained in 4. and stirred for 1 hour at room temperature. Thetrifluoroacetic acid was evaporated to obtain a trifluoroacetic acidsalt of the aforementioned compound.

6. Synthesis of(3S*,3aS*,6R*,7R*,7aS*)-1-(3-guanidinopropyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide

A trifluoroacetic acid salt of the aforementioned compound was obtainedby the same method as 5. by using(3S*,3aS*,6R*,7R*,7aS*)-1-(3-(N,N′-di(tert-butoxycarbonyl)guanidino)propyl)-7-isobutyl-N-(naphthalen-1-ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamideobtained in 4.

Synthesis of (3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyl-1,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamideand(3S*,3aR*,6S*,7R*,7aR*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyl-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6H-carboxamide

Chloroform (1 mL) was added to N-phenethyl prop-2-en-1-amine (58.4 mg,0.4 mmol), 4-((tert-butyldimethylsilyl)oxy)butanal (80.0 mg, 0.4 mmol),and molecular sieve 4 A (400 mg), and thenN-benzyl-1,2,4-triazine-3-carboxamide (43.8 mg, 0.2 mmol) and chloroform(1 mL) were further added. The reaction mixture was heated for 48 hoursat 55° C. and filtered. The filtrate was concentrated udner reducedpressure. The resulting residue was purified by preparative TLC (Merck1.13895.001, layer thickness 1 mm) (ethyl acetate:methanol=9:1) toobtain a mixture of the aforementioned compound (73.3 mg, yield 69%,RT=1.08 minutes, 1.12 minutes (C method), [M+1]⁺=532).

Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamideand(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide

The mixture obtained in the above reaction (73.3 mg) was dissolved inmethanol (1.5 mL), and sodium borohydride (9 mg, 0.24 mmol) was addedand stirred for 12 hours at room temperature. Ethyl acetate was added tothe reaction mixture, which was washed twice with saturated saline. Theorganic phase was dried with anhydrous sodium sulfate. The anhydroussodium sulfate was filtered out. The filtrate was concentrated underreduced pressure and purified by preparative TLC (Merck 1.13895.001,layer thickness 1 mm) (ethyl acetate:methanol=4:1) to obtain(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(47.6 mg, two-step yield of 43%, RT=1.13 minutes (C method), [M+1]⁺=534)and(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(20.6 mg, two-step yield of 19%, RT=0.95 minutes (C method),[M+1]⁺=534).

Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-hydroxyethyl)-1-phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3aH-carboxamide

(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-a-carboxamide(46.7 mg, 0.087 mmol) was dissolved in tetrahydrofuran (1 mL), andtetrabutylammonium fluoride (approximately 1 mol/L tetrahydrofuransolution, 0.1 mL) was added and stirred overnight at room temperature.The reaction mixture was concentrated and ethyl acetate was added, andthen transferred to a separatory funnel and washed with saturatedsaline. The organic phase was dried with anhydrous sodium sulfate,concentrated under reduced pressure, and purified by preparative TLC(Merck 1.05744.001, layer thickness 0.5 mm) (ethyl acetate:methanol=4:1)to obtain the aforementioned compound (35 mg, yield of 96%, RT=0.85minutes (C method), [M+1]⁺=420).

Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-hydroxyethyl)-1-phenethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6H-carboxamide

(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide(20.6 mg, 0.039 mmol) was dissolved in tetrahydrofuran (0.5 mL), andtetrabutylammonium fluoride (approximately 1 mol/L tetrahydrofuransolution, 0.05 mL) was added and stirred overnight at room temperature.The reaction mixture was concentrated, ethyl acetate was added andtransferred to a separatory funnel, and washed twice with saturatedsaline. The organic phase was dried with anhydrous sodium sulfate,concentrated under reduced pressure, and purified by preparative TLC(Merck 105744.001, layer thickness 0.5 mm) (ethyl acetate:methanol=4:1)to obtain the aforementioned compound (16 mg, yield of 91%, RT =0.72minutes (C method), [M+1]⁺=420).

Synthesis of(3S*,3aS*,6S*,7R*,7aS*)-N,4,7-tribenzyl-1-(naphthalen-1-ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(naphthalen-1-ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide(compound D3-42, 5 mg, 0.01 mmol) was dissolved in tetrahydrofuran (0.2mL), then benzaldehyde (2.1 mg, 0.02 mmol), trifluoroacetic acid (3.4mg, 0.03 mmol), and molecular sieve 4 A (40 mg) were added and heatedfor 18 hours at 50° C. Sodium triacetoxyborohydride (5 mg, 0.024 mmol)was added to the reaction mixture and stirred for 5 hours at roomtemperature. To the reaction mixture, ethyl acetate and saturated sodiumbicarbonate water are added. The organic phase was washed twice withsaturated saline. The organic phase was dried with anhydrous sodiumsulfate, concentrated under reduced pressure, and purified by TLC (Merck105715.001, layer thickness 0.25 mm) (hexane:ethyl acetate=2:1) toobtain the aforementioned compound (1.2 mg, yield of 20%, RT=1.14minutes (C method), [M+1]⁺=592).

Tables 3 and 4 summarize the synthedized compounds of formula IB andcompounds of IF. In the following tables, “EX” means that the synthesismethod is described in the Examples.

TABLE 3

Compound Synthesis number R₁ R₂ R₃ R₄ method Intermediate IB-1  i-BuBnzl Bnzl H EX IIB-1 IB-2  i-Bu i-Bu i-Bu H IB-1 IIB-2 IB-3  i-Bu i-BuBnzl H IB-1 IIB-3 IB-4  Bnzl i-Bu i-Bu H IB-1 IIB-4 IB-5  i-Bu Bnzl i-BuH IB-1 IIB-5 IB-6  Bnzl i-Bu Bnzl H IB-1 IIB-6 IB-7  Bnzl Bnzl i-Bu HIB-1 IIB-7 IB-8  Bnzl Bnzl Bnzl H IB-1 IIB-8 IB-9  i-Pnt Bnzl Bnzl HIB-1 IIB-9 IB-10 Bnzl Bnzl i-Pnt H IB-1 IIB-10 IB-11 i-Bu Bnzl Ph-Et HIB-1 IIB-11 IB-12 i-Bu Ph-Et Bnzl H IB-1 IIB-12 IB-13 i-Bu Bnzl 3-Me- HIB-1 IIB-13 Bnzl IB-14 i-Bu Bnzl 4-Me- H IB-1 IIB-14 Bnzl IB-15 i-Bu3-Me-Bnzl Bnzl H IB-1 IIB-15 IB-16 i-Bu 4-Me-Bnzl Bnzl H IB-1 IIB-16IB-17 i-Bu 3-Cl-Bnzl Bnzl H IB-1 IIB-17 IB-18 i-Bu 4-Cl-Bnzl Bnzl H IB-1IIB-18 IB-19 3,4-Cl₂- Bnzl i-Bu H IB-1 IIB-19 Bnzl IB-20 Bnzl3,4-Cl₂-Bnzl i-Bu H IB-1 IIB-20 IB-21 Me Np-E Bnzl H IB-1 IIB-21 IB-22i-Bu 4-OH-Bnzl Bnzl H IB-40 IB-23 IB-23 i-Bu 4-(tert- Bnzl H IB-1 IIB-23butoxy)benzyl IB-24 i-Bu Np-M Bnzl H IB-1 IIB-24 IB-25 i-Bu Hdr-E Bnzl HIB-1 IIB-25 IB-26 i-Bu Cbx-E Bnzl H IF-26 IB-27 IB-27 i-Bu2-(tert-butoxy)-2- Bnzl H IB-1 IIB-27 oxoethyl IB-28 i-Bu Cbm-E Bnzl HIB-1 IIB-28 IB-29 i-Bu 4-aminobutyl Bnzl H EX IB-30 IB-30 i-Bu 4-((tert-Bnzl H IB-1 IIB-30 butoxycarbonyl)amino) butyl IB-31 i-Bu Chm Bnzl HIB-1 IIB-31 IB-32 i-Bu (tetrahydro-2H- Bnzl H IB-1 IIB-32pyran-2-yl)methyl IB-33 i-Bu Bnzl 4- H IF-33 IB-34 amino- butyl IB-34i-Bu Bnzl 4- H IB-1 IIB-34 ((tert- butoxy carbon yl)amino) butyl IB-35i-Bu Bnzl Cbx-E H EX IB-73 IB-36 i-Bu Bnzl 3- H IB-1 IIB-36 methoxy- 3-oxopro- pyl IB-37 i-Bu Bnzl Cbm-E H IF-33 IB-75 IB-38 i-Bu Bnzl Chm HIB-1 IIB-38 IB-39 Chm Bnzl Bnzl H IB-1 IIB-39 IB-40 4-OH- Bnzl Bnzl H EXIB-41 Bnzl IB-41 4- Bnzl Bnzl H IB-1 IIB-41 (tert- butoxy) benzyl IB-42Np-M Bnzl Bnzl H IB-1 IIB-42 IB-43 i-Bu Bnzl Bnzl Ac IF-43 IB-1 IB-44i-Bu i-Bu i-Bu Ac IF-43 IB-2 IB-45 i-Bu i-Bu Bnzl Ac IF-43 IB-3 IB-46Bnzl i-Bu i-Bu Ac IF-43 IB-4 IB-47 i-Bu Bnzl i-Bu Ac IF-43 IB-5 IB-49Bnzl Bnzl i-Bu Ac IF-43 IB-7 IB-50 Bnzl Bnzl Bnzl Ac IF-43 IB-8 IB-54i-Bu Ph-Et Bnzl Ac IF-43 IB-12 IB-57 i-Bu 3-Me-Bnzl Bnzl Ac IF-43 IB-15IB-58 i-Bu 4-Me-Bnzl Bnzl Ac IF-43 IB-16 IB-64 Me Np-E Bnzl Ac IF-43IB-21 IB-68 i-Bu Bnzl Bnzl Bz EX IB-1 IB-69 i-Bu Bnzl Bnzl Et EX IB-1IB-70 i-Bu Bnzl Bnzl methoxy- EX IB-1 carbonyl IB-71 i-Bu Bnzl Bnzl MeIF-71 IB-1 IB-72 Me Np-E Bnzl Et IB-69 IB-21 IB-73 i-Bu Bnzl Cbx-E tBOCEX IB-74 IB-74 i-Bu Bnzl 3- tBOC EX IB-36 methoxy- 3- oxopropyl IB-75i-Bu Bnzl Cbm-E tBOC EX IB-73 IB-76 3- Bnzl Bnzl H IB-1 IIB-76 (tert-butoxy)- 3-oxopro- pyl IB-77 Bnzl Bnzl 4-OH- H IB-1 IIB-77 Bnzl IB-78 Me2-(1-(tert- Bnzl H IB-1 IIB-78 butoxycarbonyl)-1H- indo1-3-yl)ethylIB-79 Chm Bnzl Bnzl pro- EX IB-39 pyl carba- moyl IB-80 Np-M Bnzl Pr HIB-1 IIB-80 LCMS Compound t_(R) Mass Elution Yield number Name ofcompound (min) (M + H)⁺ condition (%) IB-1(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.21 418 B 811-isobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-2 (3S*,3aS*,6R*,7R*,7aS*)-N,1,7- 1.20 350 B 77triisobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-3 (3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N,1- 1.19 384 B 75diisobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-4 (3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-N,7- 1.20 384 B 88diisobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-5 (3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1,7- 1.20 384 B 76diisobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-6 (3S*,3aS*,6R*,7R*,7aS*)-1,7-dibenzyl- 1.20 418 B 54N-isobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-7 (3S*,3aS*,6R*,7R*,7aS*)-N,1-dibenzyl- 1.21 418 B 817-isobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-8 (3S*,3aS*,6R*,7R*,7aS*)-N,1,7- 1.21 452 B 76tribenzyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-9 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.23 432 B 811-isopentyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-10 (3S*,3aS*,6R*,7R*,7aS*)-N,1-dibenzyl- 1.23 432 B 377-isopentyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-11 (3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.22 432 B 63isobutyl-7-phenethyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-12 (3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-7- 1.23 432 B 65isobutyl-N-phenethyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-13 (3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.24 432 B 64isobutyl-7-(3-methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-14(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.23 432 B 74isobutyl-7-(4-methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-15(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.24 432 B 66isobutyl-N-(3-methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-16(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.25 432 B 72isobutyl-N-(4-methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-17(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N-(3- 1.03 452 B 85chlorobenzyl)-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-18(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N-(4- 1.24 452 B 79chlorobenzyl)-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-19(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.13 486 B 43(3,4-dichlorobenzyl)-7-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-20(3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-N- 1.26 486 B 84(3,4-dichlorobenzyl)-7- isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-21(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.19 440 B 82isobutyl-N-(2-(naphthalen-1- yl)ethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-22(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N-(4- 0.89 434 A 95hydroxybenzyl)-1-isobutyloctahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-23 (3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.06490 A 88 isobutyl-N-(4-(tert- butoxy)benzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-24(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 1.05 468 A 84isobutyl-N-(naphthalen-1- ylmethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-25(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N-(2- 0.80 372 A 77hydroxyethyl)-1-isobutyloctahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-26 3-((3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1-0.82 400 A 95 isobutyloctahydro-1H-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide)propanoic acid IB-27(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 0.99 456 A 93isobutyl-N-(2-(tert-butoxy)-2- oxoethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-28(3S*,3aS*,6R*,7R*,7aS*)-N-(3-amino-3- 0.79 399 A 80oxopropyl)-7-benzyl-1- isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-29(3S*,3aS*,6R*,7R*,7aS*)-N-(4- 0.75 399 A 100 aminobutyl)-7-benzyl-1-isobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a- carboxamideIB-30 (3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 0.97 499 A 62isobutyl-N-(4-((tert- butoxycarbonyl)amino)butyl)octahydro-3aH-3,6-methanopyrrolo[3,2- b]pyridine-3a-carboxamide IB-31(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N- 1.05 424 A 42cyclohexylmethyl-1-isobutyloctahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-32 (3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1- 0.96426 A 97 isobutyl-N-((tetrahydro-2H-pyran-2-yl)methyl)octahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-33 (3S*,3aS*,6R*,7R*,7aS*)-7-(4- 0.74 399 A 100aminobutyl)-N-benzyl-1- isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-34(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 0.99 499 A 77 isobutyl-7-(4-((tert-butoxycarbonyl)amino)butyl)octahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-35 3-((3S*,3aS*,6R*,7R*,7aS*)-3a- 0.83 400A 100 (benzylcarbamoyl)-1- isobutyloctahydro-1H-3,6-methanopyrrolo[3,2-b]pyridin-7- yl)propanoic acid IB-36(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 0.90 414 A 73isobutyl-7-(3-methoxy-3- oxopropyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-37(3S*,3aS*,6R*,7R*,7aS*)-7-(3-amino-3- 0.78 399 A 100oxopropyl)-N-benzyl-1- isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-38(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-7- 1.07 424 A 82 (cyclohexylmethyl)-1-isobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a- carboxamideIB-39 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.06 458 A 781-cyclohexylmethyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-40 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 0.89 468 A 991-(4-hydroxybenzyl)octahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-41 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.05 524 A 651-(4-(tert-butoxy)benzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-42(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.05 502 A 631-(naphthalen-1-ylmethyl)octahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-43 (3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-N,7-1.14 460 B 86 dibenzyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-44(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl- 1.10 392 B 86N,1,7-triisobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-45 (3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-7- 1.10 426 B 82benzyl-N,1-diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-46(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-1- 1.10 426 B 91benzyl-N,7-diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-47(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-N- 1.11 426 B 85benzyl-1,7-dilsobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-49(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-N,1- 1.13 460 B 86dibenzyl-7-isobutyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-50 (3S*,3aS*,6R*,7R*,7aS*)-4-acetyl- 1.16 494 B 81N,1,7-tribenzyloctahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-54 (3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-1- 1.15 474 B 82benzyl-7-isobutyl-N- phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-57(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-7- 1.17 474 B 87benzyl-1-isobutyl-N-(3- methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-58(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-7- 1.17 474 B 80benzyl-1-isobutyl-N-(4- methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-64(3S*,3aS*,6R*,7R*,7aS*)-4-acetyl-7- 1.12 482 B 100benzyl-1-isobutyl-N-(2-(naphthalen- 1-yl)ethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-68(3S*,3aS*,6R*,7R*,7aS*)-4-benzoyl- 1.23 522 B 39N,7-dibenzyl-1-isobutyloctahydro- 3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-69 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1.24 446 B 28 4-ethyl-1-isobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine- 3a-carboxamide IB-70(3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.18 476 B 85 1-isobutyl-4-(methoxycarbonyl)octahydro-3aH-3,6- methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-71 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl- 1.22 432 B 351-isobutyl-4-methyloctahydro-3aH- 3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-72 (3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-4- 1.24 468 B 70ethyl-1-isobutyl-N-(2-(naphthalen- 1-yl)ethyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide IB-73 tert-butyl(3S*,3aS*,6R*,7R*,7aS*)- 0.91 500 A 1003a-(benzylcarbamoyl)-1-isobutyl-7- (2-carboxyethyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridlne-4- carboxylate IB-74 tert-butyl(3S*,3aS*,6R*,7R*,7aS*)- 0.97 514 A 753a-(benzylcarbamoyl)-1-isobutyl-7- (3-methoxy-3-oxopropyl)octahydro-4H-3,6-methanopyrrolo[3,2- b]pyridine-4-carboxylate IB-75 tert-butyl(3S*,3aS*,6R*,7R*,7aS*)- 0.86 499 A 263a-(benzylcarbamoyl)-1-isobutyl-7- (3-amino-3-oxopropyl)octahydro-4H-3,6-methanopyrrolo[3,2-b]pyridine- 4-carboxylate IB-76 tert-butyl 3-1.20 490 B 68 ((3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-3a-(benzylcarbamoyl)octahydro-1H-3,6- methanopyrrolo[3,2-b]pyridin-1-yl)propanoate IB-77 (3S*,3aS*,6R*,7R*,7aS*)-N,1-dibenzyl- 1.13 468 B 607-(4-hydroxybenzyl)octahydro-3aH- 3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-78 tert-butyl 3- 1.25 529 B 71((3S*,3aS*,6R*,7R*,7aS*)-2-(7-benzyl- 1-methyloctahydro-1H-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide)ethyl)-1H-indole-1-carboxylate IB-79 (3S*,3aS*,6R*,7R*,7aS*)-N^(3a),7- 1.05 543 A 65dibenzyl-1-(cyclohexylmethyl)-N⁴- propylhexahydro-1H-3,6-methanopyrrolo[3,2-b]pyridine-3a,4- dicarboxamide IB-80(3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1- 1.02 454 A 62(naphthalen-1-ylmethyl)-7- propyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a- carboxamide

Time of reten- Compound tion Mass Measurement number R₁ R₂ R₃ TR (min)(M + H)⁺ condition IB-81  Cbm-M Np-M i-Bu 0.79 435 C IB-82  Cbm-M Np-MBnzl 0.80 469 C IB-83  Cbm-M Np-M 4-OH-Bnzl 0.75 485 C IB-84  Cbm-M Np-Mi-Pnt 0.83 449 C IB-85  Cbm-M Np-M Ph-Et 0.83 483 C IB-86  Cbm-M Ph-Eti-Bu 0.74 399 C IB-87  Cbm-M Ph-Et Bnzl 0.75 433 C IB-88  Cbm-M Ph-Et4-OH-Bnzl 0.69 449 C IB-89  Cbm-M Ph-Et i-Pnt 0.78 413 C IB-90  Cbm-MNp-M Np-M 0.84 519 C IB-91  Cbm-M 4-F-Bnzl i-Bu 0.74 403 C IB-92  Cbm-M4-F-Bnzl Bnzl 0.75 437 C IB-93  Cbm-M 4-F-Bnzl 4-OH-Bnzl 0.69 453 CIB-94  Cbm-M 4-F-Bnzl i-Pnt 0.78 417 C IB-95  Cbm-M 4-F-Bnzl Ph-Et 0.78451 C IB-96  Cbm-M 4-F-Bnzl Np-M 0.80 487 C IB-97  Cbm-M Ph-Et Np-M 0.82483 C IB-98  Cbm-M i-Pnt i-Bu 0.73 365 C IB-99  Cbm-M i-Pnt Bnzl 0.74399 C IB-100 Cbm-M i-Pnt 4-OH-Bnzl 0.70 415 C IB-101 Cbm-M i-Pnt Cbx-E0.64 381 C IB-102 Cbm-M i-Pnt Ph-Et 0.78 413 C IB-103 Cbm-M i-Pnt Np-M0.80 449 C IB-104 Cbm-M Hxy i-Bu 0.78 379 C IB-105 Cbm-M Hxy Bnzl 0.79413 C IB-106 Cbm-M Hxy 4-OH-Bnzl 0.74 429 C IB-107 Cbm-M Hxy Cbx-E 0.70395 C IB-108 Cbm-M Hxy i-Pnt 0.82 393 C IB-109 Cbm-M Hxy Ph-Et 0.82 427C IB-110 Cbm-M Hxy Np-M 0.84 463 C IB-111 Cbm-M i-Pr i-Bu 0.65 337 CIB-112 Cbm-M i-Pr Bnzl 0.66 371 C IB-113 Cbm-M i-Pr 4-OH-Bnzl 0.59 387 CIB-114 Cbm-M i-Pr Cbx-E 0.98 353 D IB-115 Cbm-M i-Pr i-Pnt 0.70 351 CIB-116 Cbm-M i-Pr Ph-Et 0.72 385 C IB-117 Cbm-M i-Pr Np-M 0.74 421 CIB-118 Cbm-M i-Bu i-Bu 0.71 351 C IB-119 Cbm-M i-Bu Bnzl 0.72 385 CIB-120 Cbm-M i-Bu 4-OH-Bnzl 0.65 401 C IB-121 Cbm-M i-Bu Cbx-E 0.60 367C IB-122 Cbm-M i-Bu i-Pnt 0.76 365 C IB-123 Cbm-M i-Bu Ph-Et 0.77 399 CIB-124 Cbm-M i-Bu Np-M 0.79 435 C IB-125 Cbm-M Bnzl i-Bu 0.74 385 CIB-126 Cbm-M Bnzl Bnzl 0.75 419 C IB-127 Cbm-M Bnzl 4-OH-Bnzl 0.69 435 CIB-128 Cbm-M Bnzl Cbx-E 0.63 401 C IB-129 Cbm-M Bnzl i-Pnt 0.79 399 CIB-130 Cbm-M Bnzl Ph-Et 0.80 433 C IB-131 Cbm-M Bnzl Np-M 0.81 469 CIB-132 Cbm-M 4-OH-Bnzl i-Bu 0.67 401 C IB-133 Cbm-M 4-OH-Bnzl Bnzl 0.69435 C IB-134 Cbm-M 4-OH-Bnzl Cbx-E 0.98 417 D IB-135 Cbm-M 4-OH-Bnzli-Pnt 0.73 415 C IB-136 Cbm-M 4-OH-Bnzl Ph-Et 0.74 449 C IB-137 Cbm-M4-OH-Bnzl Np-M 0.76 485 C IB-138 Cbm-M Cbx-E i-Bu 0.61 367 C IB-139Cbm-M Cbx-E Bnzl 0.62 401 C IB-140 Cbm-M Cbx-E 4-OH-Bnzl 0.98 417 DIB-141 Cbm-M Cbx-E i-Pnt 0.67 381 C IB-142 Cbm-M Cbx-E Ph-Et 0.69 415 CIB-143 Cbm-M Cbx-E Np-M 0.71 451 C IB-144 Cbm-M Cbm-E i-Bu 0.59 366 CIB-145 Cbm-M Cbm-E Bnzl 0.61 400 C IB-146 Cbm-M Cbm-E 4-OH-Bnzl 0.97 416D IB-147 Cbm-M Cbm-E Cbx-E 0.20 382 E IB-148 Cbm-M Cbm-E i-Pnt 0.65 380C IB-149 Cbm-M Cbm-E Ph-Et 0.67 414 C IB-150 Cbm-M Cbm-E Np-M 0.69 450 CIB-151 Cbm-M Gun-Pr i-Bu 0.59 394 C IB-152 Cbm-M Gun-Pr Bnzl 0.60 428 CIB-153 Cbm-M Gun-Pr 4-OH-Bnzl 0.91 444 D IB-154 Cbm-M Gun-Pr i-Pnt 0.63408 C IB-155 Cbm-M Gun-Pr Ph-Et 0.65 442 C IB-156 Cbm-M Gun-Pr Np-M 1.15478 D IB-157 Cbm-M Hdr-E i-Bu 0.60 339 C IB-158 Cbm-M Hdr-E Bnzl 0.61373 C IB-159 Cbm-M Hdr-E 4-OH-Bnzl 0.98 389 D IB-160 Cbm-M Hdr-E Cbx-E0.20 355 E IB-161 Cbm-M Hdr-E i-Pnt 0.65 353 C IB-162 Cbm-M Hdr-E Ph-Et0.67 387 C IB-163 Cbm-M Hdr-E Np-M 0.70 423 C IB-164 Gun-Pr Np-M i-Bu1.25 477 D IB-165 Gun-Pr Np-M Bnzl 0.73 511 C IB-166 Gun-Pr Np-M4-OH-Bnzl 0.71 527 C IB-167 Gun-Pr Np-M i-Pnt 1.30 491 D IB-168 Gun-PrNp-M Ph-Et 1.31 525 D IB-169 Gun-Pr Np-M Np-M 1.31 561 D IB-170 Gun-PrHxy i-Bu 0.74 421 C IB-171 Gun-Pr Hxy Bnzl 0.74 455 C IB-172 Gun-Pr Hxy4-OH-Bnzl 1.23 471 D IB-173 Gun-Pr Hxy i-Pnt 0.77 435 C IB-174 Gun-PrHxy Ph-Et 1.33 469 D IB-175 Gun-Pr Hxy Np-M 1.32 505 D IB-176 Gun-Pri-Pr i-Bu 1.08 379 D IB-177 Gun-Pr i-Pr 4-OH-Bnzl 1.04 429 D IB-178Gun-Pr i-Pr i-Pnt 1.15 393 D IB-179 Gun-Pr i-Pr Ph-Et 1.17 427 D IB-180Gun-Pr i-Pr Np-M 1.18 463 D IB-181 Gun-Pr 4-F-Bnzl i-Bu 1.19 445 DIB-182 Gun-Pr 4-F-Bnzl Bnzl 0.70 479 C IB-183 Gun-Pr 4-F-Bnzl 4-OH-Bnzl1.14 495 D IB-184 Gun-Pr 4-F-Bnzl i-Pnt 1.26 459 D IB-185 Gun-Pr4-F-Bnzl Ph-Et 0.74 493 C IB-186 Gun-Pr 4-F-Bnzl Np-M 0.74 529 C IB-187i-Bu i-Bu Gun-Pr 3.80 393 G IB-188 i-Bu Bnzl Gun-Pr 4.09 427 G IB-189i-Bu 4-OH-Bnzl Gun-Pr 3.67 443 G IB-190 i-Bu Cbm-E Gun-Pr 3.04 408 GIB-191 i-Bu Hdr-E Gun-Pr 3.00 381 G IB-192 i-Bu i-Pnt Gun-Pr 4.15 407 GIB-193 i-Bu Ph-Et Gun-Pr 4.30 441 G IB-194 i-Bu Np-M Gun-Pr 4.70 477 GIB-195 i-Bu Hxy Gun-Pr 4.54 421 G IB-196 i-Bu i-Pr Gun-Pr 3.72 379 GIB-197 i-Bu 4-F-Bnzl Gun-Pr 4.29 445 G IB-198 Bnzl i-Bu Gun-Pr 2.65 427F IB-199 Bnzl 4-OH-Bnzl Gun-Pr 3.88 477 G IB-200 Bnzl Cbm-E Gun-Pr 3.17442 G IB-201 Bnzl Hdr-E Gun-Pr 3.20 415 G IB-202 Bnzl i-Pr Gun-Pr 3.82413 F IB-203 4-OH-Bnzl i-Bu Gun-Pr 3.65 443 G IB-204 4-OH-Bnzl i-PntGun-Pr 3.92 457 G IB-205 4-OH-Bnzl Ph-Et Gun-Pr 3.95 491 G IB-2064-OH-Bnzl Np-M Gun-Pr 4.32 527 G IB-207 4-OH-Bnzl 4-F-Bnzl Gun-Pr 3.94495 G IB-208 i-Pnt i-Bu Gun-Pr 2.54 407 F IB-209 i-Pnt Bnzl Gun-Pr 2.65441 F IB-210 i-Pnt 4-OH-Bnzl Gun-Pr 2.43 457 F IB-211 i-Pnt Cbm-E Gun-Pr3.07 422 G IB-212 i-Pnt Hdr-E Gun-Pr 3.07 395 G IB-213 i-Pnt Ph-EtGun-Pr 2.75 455 F IB-214 i-Pnt Np-M Gun-Pr 3.07 491 F IB-215 i-Pnt HxyGun-Pr 2.84 435 F IB-216 i-Pnt i-Pr Gun-Pr 3.59 393 G IB-217 i-Pnt4-F-Bnzl Gun-Pr 2.74 459 F IB-218 Ph-Et Hdr-E Gun-Pr 3.63 429 G IB-219Np-M i-Bu Gun-Pr 3.02 477 F IB-220 Np-M Bnzl Gun-Pr 4.80 511 G IB-221Np-M 4-OH-Bnzl Gun-Pr 4.35 527 G IB-222 Np-M Cbm-E Gun-Pr 3.85 492 GIB-223 Np-M Hdr-E Gun-Pr 3.92 465 G IB-224 Np-M i-Pnt Gun-Pr 3.22 491 FIB-225 Np-M Ph-Et Gun-Pr 3.10 525 F IB-226 Np-M Np-M Gun-Pr 3.24 561 FIB-227 Np-M Hxy Gun-Pr 5.09 505 G IB-228 Np-M i-Pr Gun-Pr 2.82 463 FIB-229 Np-M 4-F-Bnzl Gun-Pr 4.87 529 G IB-230 Chm i-Bu Gun-Pr 2.82 433 FIB-231 Chm Bnzl Gun-Pr 2.95 467 F IB-232 Chm 4-OH-Bnzl Gun-Pr 2.67 483 FIB-233 Chm Cbm-E Gun-Pr 3.49 448 G IB-234 Chm Hdr-E Gun-Pr 3.50 421 GIB-235 Chm i-Pnt Gun-Pr 3.04 447 F IB-236 Chm Ph-Et Gun-Pr 2.94 481 FIB-237 Chm Np-M Gun-Pr 3.22 517 F IB-238 Chm Hxy Gun-Pr 3.15 461 FIB-239 Chm i-Pr Gun-Pr 2.69 419 F IB-240 Chm 4-F-Bnzl Gun-Pr 2.99 485 FIB-241 4-F-Bnzl 4-OH-Bnzl Gun-Pr 4.00 495 G IB-242 4-F-Bnzl Cbm-E Gun-Pr3.29 460 G IB-243 4-F-Bnzl Hdr-E Gun-Pr 3.27 433 F IB-244 4-F-Bnzl i-PrGun-Pr 3.84 431 G IB-245 Bnzl Bnzl Gun-Pr 2.69 461 F IB-246 Bnzl i-PntGun-Pr 2.74 441 F IB-247 Bnzl Ph-Et Gun-Pr 2.77 475 F IB-248 Bnzl Np-MGun-Pr 3.07 511 F IB-249 Bnzl Hxy Gun-Pr 2.97 455 F IB-250 Bnzl 4-F-BnzlGun-Pr 2.77 479 F IB-251 Ph-Et i-Bu Gun-Pr 2.75 441 F IB-252 Ph-Et BnzlGun-Pr 2.85 475 F IB-253 Ph-Et 4-OH-Bnzl Gun-Pr 2.60 491 F IB-254 Ph-Eti-Pnt Gun-Pr 2.85 455 F IB-255 Ph-Et Np-M Gun-Pr 3.25 525 F IB-256 Ph-EtHxy Gun-Pr 3.15 469 F IB-257 Ph-Et i-Pr Gun-Pr 2.52 427 F IB-258 Ph-Et4-F-Bnzl Gun-Pr 2.97 493 F IB-259 4-F-Bnzl i-Bu Gun-Pr 2.67 445 F IB-2604-F-Bnzl Bnzl Gun-Pr 2.80 479 F IB-261 4-F-Bnzl i-Pnt Gun-Pr 2.84 459 FIB-262 4-F-Bnzl Ph-Et Gun-Pr 2.88 493 F IB-263 4-F-Bnzl Np-M Gun-Pr 3.20529 F IB-264 4-F-Bnzl Hxy Gun-Pr 3.04 473 F IB-265 i-Bu Cbm-E Cbx-E 2.06381 H IB-266 i-Bu Cbm-E i-Pnt 2.48 379 H IB-267 i-Bu Gun-Pr i-Bu 2.35393 H IB-268 i-Bu Gun-Pr Bnzl 2.39 427 H IB-269 i-Bu Gun-Pr 4-OH-Bnzl1.98 443 H IB-270 i-Bu Gun-Pr i-Pnt 2.24 407 H IB-271 i-Bu Gun-Pr Ph-Et2.25 441 H IB-272 i-Bu Gun-Pr Np-M 2.28 477 H IB-273 Bnzl Cbm-E Cbx-E1.90 415 H IB-274 Bnzl Cbm-E i-Pnt 2.28 413 H IB-275 Bnzl Gun-Pr i-Bu2.17 427 H IB-276 Bnzl Gun-Pr Bnzl 2.25 461 H IB-277 Bnzl Gun-Pr4-OH-Bnzl 2.07 477 H IB-278 Bnzl Gun-Pr i-Pnt 2.36 441 H IB-279 BnzlGun-Pr Ph-Et 2.28 475 H IB-280 Bnzl Gun-Pr Np-M 2.33 511 H IB-2814-OH-Bnzl Cbm-E Cbx-E 1.71 431 H IB-282 4-OH-Bnzl Cbm-E i-Pnt 2.03 429 HIB-283 4-OH-Bnzl Gun-Pr i-Bu 1.96 443 H IB-284 4-OH-Bnzl Gun-Pr Bnzl2.12 477 H IB-285 4-OH-Bnzl Gun-Pr i-Pnt 2.03 457 H IB-286 4-OH-BnzlGun-Pr Ph-Et 2.13 491 H IB-287 4-OH-Bnzl Gun-Pr Np-M 2.22 527 H IB-288Cbx-E Cbm-E i-Pnt 2.10 395 H IB-289 Gun-Pr i-Bu i-Bu 2.02 393 H IB-290Gun-Pr i-Bu Bnzl 2.01 427 H IB-291 Gun-Pr i-Bu 4-OH-Bnzl 1.95 443 HIB-292 Gun-Pr i-Bu i-Pnt 2.04 407 H IB-293 Gun-Pr i-Bu Ph-Et 2.12 441 HIB-294 Gun-Pr i-Bu Np-M 2.14 477 H IB-295 Gun-Pr Bnzl i-Bu 2.03 427 HIB-296 Gun-Pr Bnzl Bnzl 2.06 461 H IB-297 Gun-Pr Bnzl 4-OH-Bnzl 1.98 477H IB-298 Gun-Pr Bnzl i-Pnt 2.16 441 H IB-299 Gun-Pr Bnzl Ph-Et 2.19 475H IB-300 Gun-Pr Bnzl Np-M 2.21 511 H IB-301 Gun-Pr 4-OH-Bnzl i-Bu 1.93443 H IB-302 Gun-Pr 4-OH-Bnzl Bnzl 1.95 477 H IB-303 Gun-Pr 4-OH-Bnzli-Pnt 2.05 457 H IB-304 Gun-Pr 4-OH-Bnzl Ph-Et 2.07 491 H IB-305 Gun-Pr4-OH-Bnzl Np-M 2.11 527 H IB-306 Gun-Pr Cbm-E i-Bu 1.83 408 H IB-307Gun-Pr Cbm-E Bnzl 1.85 442 H IB-308 Gun-Pr Cbm-E 4-OH-Bnzl 1.75 458 HIB-309 Gun-Pr Cbm-E i-Pnt 1.91 422 H IB-310 Gun-Pr Cbm-E Ph-Et 1.96 456H IB-311 Gun-Pr Cbm-E Np-M 1.98 492 H IB-312 Gun-Pr Hdr-E i-Bu 1.81 381H IB-313 Gun-Pr Hdr-E Bnzl 1.85 415 H IB-314 Gun-Pr Hdr-E 4-OH-Bnzl 1.73431 H IB-315 Gun-Pr Hdr-E i-Pnt 1.92 395 H IB-316 Gun-Pr Hdr-E Ph-Et1.94 429 H IB-317 Gun-Pr Hdr-E Np-M 1.98 465 H IB-318 Gun-Pr i-Pnt i-Bu2.10 407 H IB-319 Gun-Pr i-Pnt Bnzl 2.11 441 H IB-320 Gun-Pr i-Pnt4-OH-Bnzl 2.03 457 H IB-321 Gun-Pr i-Pnt Ph-Et 2.12 455 H IB-322 Gun-Pri-Pnt Np-M 2.22 491 H IB-323 Gun-Pr Ph-Et i-Bu 2.12 441 H IB-324 Gun-PrPh-Et Bnzl 2.09 475 H IB-325 Gun-Pr Ph-Et 4-OH-Bnzl 2.02 491 H IB-326Gun-Pr Ph-Et i-Pnt 2.18 455 H IB-327 Gun-Pr Ph-Et Np-M 2.25 525 H IB-328Hdr-E Cbm-E i-Pnt 1.98 367 H IB-329 Hdr-E Gun-Pr i-Bu 1.89 381 H IB-330Hdr-E Gun-Pr Bnzl 1.96 415 H IB-331 Hdr-E Gun-Pr 4-OH-Bnzl 1.84 431 HIB-332 Hdr-E Gun-Pr i-Pnt 2.00 395 H IB-333 Hdr-E Gun-Pr Ph-Et 2.03 429H IB-334 Hdr-E Gun-Pr Np-M 1.83 465 H IB-335 i-Pnt Cbm-E Cbx-E 1.85 395H IB-336 i-Pnt Gun-Pr i-Bu 2.14 408 H IB-337 i-Pnt Gun-Pr Bnzl 2.17 441H IB-338 i-Pnt Gun-Pr 4-OH-Bnzl 1.92 457 H IB-339 i-Pnt Gun-Pr Ph-Et2.26 455 H IB-340 i-Pnt Gun-Pr Np-M 2.31 491 H IB-341 Ph-Et Cbm-E Cbx-E2.00 429 H IB-342 Ph-Et Cbm-E i-Pnt 2.39 427 H IB-343 Ph-Et Gun-Pr i-Bu2.22 441 H IB-344 Ph-Et Gun-Pr Bnzl 2.27 475 H IB-345 Ph-Et Gun-Pr4-OH-Bnzl 2.10 491 H IB-346 Ph-Et Gun-Pr i-Pnt 2.33 455 H IB-347 Ph-EtGun-Pr Np-M 2.38 525 H IB-348 Np-M Cbm-E Cbx-E 2.14 465 H IB-349 Np-MCbm-E i-Pnt 2.57 463 H IB-350 Np-M Gun-Pr i-Bu 2.33 477 H IB-351 Np-MGun-Pr Bnzl 2.31 511 H IB-352 Np-M Gun-Pr 4-OH-Bnzl 2.18 527 H IB-353Np-M Gun-Pr i-Pnt 2.42 491 H IB-354 Np-M Gun-Pr Ph-Et 2.38 525 H IB-355Np-M Gun-Pr Np-M 2.41 561 H IB-356 Chm Cbm-E Cbx-E 2.00 421 H IB-357 ChmCbm-E i-Pnt 2.41 419 H IB-358 Chm Gun-Pr i-Bu 2.27 433 H IB-359 ChmGun-Pr Bnzl 2.31 467 H IB-360 Chm Gun-Pr 4-OH-Bnzl 2.13 483 H IB-361 ChmGun-Pr i-Pnt 2.33 447 H IB-362 Chm Gun-Pr Ph-Et 2.34 481 H IB-363 ChmGun-Pr Np-M 2.42 517 H IB-364 4-F-Bnzl Cbm-E Cbx-E 1.93 433 H IB-3654-F-Bnzl Cbm-E i-Pnt 2.29 431 H IB-366 4-F-Bnzl Gun-Pr i-Bu 2.21 445 HIB-367 4-F-Bnzl Gun-Pr Bnzl 2.26 478 H IB-368 4-F-Bnzl Gun-Pr 4-OH-Bnzl2.09 495 H IB-369 4-F-Bnzl Gun-Pr i-Pnt 2.27 459 H IB-370 4-F-BnzlGun-Pr Ph-Et 2.28 493 H IB-371 4-F-Bnzl Gun-Pr Np-M 2.36 529 H IB-372Hdr-E i-Bu i-Pnt 1.68 352 I IB-373 Ph-Et i-Bu i-Pnt 2.16 412 I IB-374Np-M i-Bu i-Pnt 2.21 448 I IB-375 Chm i-Bu i-Pnt 2.28 404 I IB-3764-F-Bnzl i-Bu i-Pnt 2.09 416 I IB-377 Bnzl i-Bu i-Pnt 2.09 398 I IB-378i-Bu i-Bu i-Pnt 2.06 364 I IB-379 Hdr-E Cbx-E i-Bu 1.33 354 I IB-380Hdr-E 4-OH-Bnzl Cbx-E 1.11 404 I IB-381 i-Pnt Cbx-E Np-M 1.87 464 IIB-382 Chm Cbx-E i-Bu 1.87 406 I IB-383 Chm 4-OH-Bnzl Cbx-E 1.68 456 IIB-384 4-F-Bnzl Cbx-E Np-M 1.90 502 I IB-385 4-F-Bnzl 4-OH-Bnzl Cbx-E1.53 468 I IB-386 i-Pnt 4-F-Bnzl Cbx-E 1.85 432 I IB-387 Ph-Et Hdr-ECbx-E 1.37 402 I IB-388 Np-M Hdr-E Cbx-E 1.54 438 I IB-389 Chm Np-MCbx-E 1.99 490 I IB-390 4-F-Bnzl Np-M Cbx-E 1.86 502 I IB-391 Cbx-EHdr-E Bnzl 1.35 388 I IB-392 Cbx-E Np-M i-Bu 1.80 450 I IB-393 Cbx-E HxyBnzl 1.79 428 I IB-394 Cbx-E 4-F-Bnzl Bnzl 1.70 452 I IB-395 Cbx-E Hdr-Ei-Pnt 1.46 368 I IB-396 Cbx-E Hdr-E Ph-Et 1.45 402 I IB-397 Cbx-E Hdr-ENp-M 1.59 438 I IB-398 Cbx-E Np-M i-Pnt 1.83 464 I IB-399 Cbx-E 4-F-Bnzli-Pnt 1.82 432 I IB-400 Cbx-E i-Bu Bnzl 1.53 400 I IB-401 Cbx-E Cbm-EPh-Et 1.49 429 I IB-402 Cbx-E 4-OH-Bnzl i-Pnt 1.60 430 I IB-403 BnzlHdr-E Cbx-E 1.31 388 I IB-404 Bnzl Hxy Cbx-E 1.88 428 I IB-405 Bnzl4-OH-Bnzl Cbx-E 1.54 450 I IB-406 i-Bu Hxy Cbx-E 1.88 394 I IB-407 i-BuCbx-E i-Bu 1.62 366 I IB-408 i-Bu i-Bu Cbx-E 1.71 366 I IB-409 i-Bu4-OH-Bnzl Cbx-E 1.47 416 I IB-410 4-OH-Bnzl Cbx-E Np-M 1.70 500 I IB-411Ph-Et i-Bu Np-M 2.32 482 I IB-412 Ph-Et 4-OH-Bnzl Np-M 2.02 532 I IB-413Np-M i-Bu Ph-Et 2.23 482 I IB-414 Np-M i-Bu Np-M 2.25 518 I IB-415 Np-Mi-Bu Bnzl 2.15 468 I IB-416 Np-M 4-OH-Bnzl Ph-Et 2.08 532 I IB-417 Np-M4-OH-Bnzl Np-M 2.11 568 I IB-418 4-F-Bnzl i-Bu Np-M 2.15 486 I IB-4194-F-Bnzl Ph-Et Np-M 2.17 534 I IB-420 Bnzl i-Bu Np-M 2.17 468 I IB-421Bnzl 4-OH-Bnzl Ph-Et 1.92 482 I IB-422 i-Bu 4-OH-Bnzl Ph-Et 1.93 448 IIB-423 4-OH-Bnzl Ph-Et Np-M 1.97 532 I IB-424 4-OH-Bnzl i-Bu i-Pnt 1.82414 I IB-425 Hdr-E Np-M Cbx-E 1.55 438 I IB-426 i-Pnt Np-M Hdr-M 1.91422 I IB-427 4-F-Bnzl Np-M Hdr-M 1.96 460 I IB-428 Cbx-E Ph-Et 4-OH-Bnzl1.59 464 I IB-429 Cbx-E Np-M Hdr-M 1.55 424 I IB-430 Cbx-E i-Bu Ph-Et1.66 414 I IB-431 Cbx-E i-Bu Hdr-M 1.21 340 I IB-432 Cbx-E i-Bu4-OH-Bnzl 1.40 416 I IB-433 Cbx-E Cbm-E Np-M 1.56 465 I IB-434 Cbx-ECbm-E Bnzl 1.41 415 I IB-435 Cbx-E Cbm-E i-Bu 1.37 381 I IB-436 Cbx-ECbm-E 4-OH-Bnzl 1.19 431 I IB-437 i-Bu Np-M Cbx-E 1.86 450 I IB-4384-OH-Bnzl Ph-Et Cbx-E 1.60 464 I IB-439 4-OH-Bnzl Np-M Cbx-E 1.69 500 IIB-440 4-OH-Bnzl Np-M Hdr-M 1.70 458 I IB-441 Hdr-E Cbm-E 4-OH-Bnzl 1.18403 I IB-442 Hdr-E 4-OH-Bnzl i-Pnt 1.58 402 I IB-443 Hdr-E 4-OH-BnzlPh-Et 1.60 436 I IB-444 Hdr-E 4-OH-Bnzl Bnzl 1.52 422 I IB-445 i-Pnt4-OH-Bnzl Np-M 2.02 498 I IB-446 i-Pnt 4-OH-Bnzl i-Bu 1.90 414 I IB-447Ph-Et 4-OH-Bnzl i-Pnt 2.02 462 I IB-448 Ph-Et 4-OH-Bnzl Bnzl 1.93 482 IIB-449 Ph-Et 4-OH-Bnzl i-Bu 1.90 448 I IB-450 Np-M 4-OH-Bnzl i-Pnt 2.08498 I IB-451 Np-M 4-OH-Bnzl Bnzl 1.99 518 I IB-452 Np-M 4-OH-Bnzl i-Bu2.00 484 I IB-453 Chm 4-OH-Bnzl i-Pnt 2.11 454 I IB-454 Chm 4-OH-BnzlPh-Et 2.08 488 I IB-455 Chm 4-OH-Bnzl Np-M 2.13 524 I IB-456 Chm4-OH-Bnzl Bnzl 2.02 474 I IB-457 4-F-Bnzl 4-OH-Bnzl Np-M 2.02 536 IIB-458 4-F-Bnzl 4-OH-Bnzl i-Bu 1.87 452 I IB-459 Np-M Hdr-E 4-OH-Bnzl1.64 472 I IB-460 Chm Hdr-E Bnzl 1.94 412 I IB-461 Ph-Et Hdr-E i-Pnt1.86 400 I IB-462 Bnzl 4-OH-Bnzl i-Pnt 1.94 448 I IB-463 Bnzl 4-OH-BnzlBnzl 1.86 468 I IB-464 Bnzl 4-OH-Bnzl i-Bu 1.84 434 I IB-465 i-Bu4-OH-Bnzl i-Pnt 1.96 414 I IB-466 i-Bu 4-OH-Bnzl Np-M 2.00 484 I IB-467i-Bu 4-OH-Bnzl i-Bu 1.85 400 I IB-468 4-OH-Bnzl Hdr-E i-Bu 1.40 388 IIB-469 4-OH-Bnzl Hdr-E i-Pnt 1.55 402 I IB-470 Hdr-E 4-OH-Bnzl Np-M 1.68472 I IB-471 Ph-Et i-Pr 4-OH-Bnzl 1.24 434 I IB-472 Np-M Bnzl 4-OH-Bnzl1.98 518 I IB-473 Chm i-Pr 4-OH-Bnzl 1.20 426 I IB-474 4-F-Bnzl BnzlNp-M 2.16 520 I IB-475 4-F-Bnzl i-Pr 4-OH-Bnzl 1.13 428 I IB-476 Hdr-EHxy Bnzl 1.92 400 I IB-477 Hdr-E Hxy i-Bu 1.87 366 I IB-478 Hdr-E Hxy4-OH-Bnzl 1.79 416 I IB-479 Hdr-E 4-F-Bnzl Bnzl 1.73 424 I IB-480 i-PntHxy 4-OH-Bnzl 2.07 442 I IB-481 i-Pnt 4-F-Bnzl 4-OH-Bnzl 1.93 466 IIB-482 Np-M Hxy i-Bu 2.35 I IB-483 Np-M Hxy 4-OH-Bnzl 2.17 512 I IB-484Chm Ph-Et Bnzl 2.36 I IB-485 Chm Hxy Bnzl 2.42 I IB-486 Chm Hxy i-Bu2.44 I IB-487 Chm Hxy 4-OH-Bnzl 2.18 468 I IB-488 Chm 4-F-Bnzl i-Bu 2.22442 I IB-489 4-F-Bnzl Ph-Et Bnzl 2.18 484 I IB-490 Hdr-E Hxy i-Pnt 1.99380 I IB-491 Hdr-E Hxy Np-M 1.98 450 I IB-492 Hdr-E 4-F-Bnzl Ph-Et 1.80438 I IB-493 Np-M Hdr-E Np-M 1.99 506 I IB-494 Chm Hxy i-Pnt 2.54 IIB-495 i-Bu Ph-Et i-Bu 2.16 398 I IB-496 i-Bu Hxy 4-OH-Bnzl 2.04 428 IIB-497 i-Bu 4-F-Bnzl i-Bu 2.05 402 I IB-498 i-Bu 4-F-Bnzl 4-OH-Bnzl 1.89452 I IB-499 4-OH-Bnzl 4-F-Bnzl i-Bu 1.91 452 I IB-500 4-OH-Bnzl BnzlNp-M 1.92 518 I IB-501 4-OH-Bnzl i-Pr i-Pnt 1.77 400 I IB-502 4-OH-Bnzli-Pr Np-M 1.83 470 I IB-503 Hdr-E Bnzl Cbx-E 1.37 388 I IB-504 Hdr-Ei-Bu Cbx-E 1.28 354 I IB-505 i-Pnt Bnzl Cbx-E 1.79 414 I IB-506 i-Pnti-Bu Cbx-E 1.75 380 I IB-507 i-Pnt 4-OH-Bnzl Cbx-E 1.49 430 I IB-508Ph-Et i-Bu Cbx-E 1.71 414 I IB-509 Np-M i-Bu Cbx-E 1.93 450 I IB-510 Chmi-Bu Cbx-E 1.91 406 I IB-511 4-F-Bnzl i-Pnt Cbx-E 1.88 432 I IB-512Cbx-E i-Pnt 4-OH-Bnzl 1.55 430 I IB-513 Cbx-E i-Pnt Ph-Et 1.71 428 IIB-514 Cbx-E i-Pnt Np-M 1.83 464 I IB-515 Cbx-E 4-OH-Bnzl Ph-Et 1.63 464I IB-516 Cbx-E 4-OH-Bnzl Np-M 1.68 500 I IB-517 i-Bu Cbx-E Np-M 1.81 450I IB-518 4-OH-Bnzl i-Pnt Cbx-E 1.61 430 I IB-519 Hdr-E Cbm-E Np-M 1.54437 I IB-520 Np-M Cbm-E i-Bu 1.83 449 I IB-521 Np-M Cbm-E 4-OH-Bnzl 1.64499 I IB-522 Chm Cbm-E Np-M 1.95 489 I IB-523 Chm Cbm-E 4-OH-Bnzl 1.57455 I IB-524 4-F-Bnzl Cbm-E Ph-Et 1.78 465 I IB-525 4-F-Bnzl Cbm-E Np-M1.86 501 I IB-526 Hdr-E Ph-Et 4-OH-Bnzl 1.53 436 I IB-527 Hdr-E Np-M4-OH-Bnzl 1.69 I IB-528 Chm Np-M i-Bu 2.35 474 I IB-529 Chm 4-F-Bnzl4-OH-Bnzl 1.99 492 I IB-530 4-F-Bnzl Np-M 4-OH-Bnzl 1.98 536 I IB-531Hdr-E Ph-Et i-Pnt 1.80 400 I IB-532 4-F-Bnzl Np-M i-Pnt 2.24 500 IIB-533 Bnzl 4-F-Bnzl i-Bu 2.07 436 I IB-534 Bnzl 4-F-Bnzl 4-OH-Bnzl 1.88486 I IB-535 Bnzl Cbm-E Ph-Et 1.73 447 I IB-536 i-Bu Ph-Et 4-OH-Bnzl1.85 448 I IB-537 i-Bu Np-M 4-OH-Bnzl 1.99 484 I IB-538 i-Bu Np-M i-Pnt2.28 448 I IB-539 i-Bu Cbm-E Ph-Et 1.71 413 I IB-540 4-OH-Bnzl Ph-Eti-Bu 1.80 448 I IB-541 4-OH-Bnzl Np-M i-Bu 1.94 484 I IB-542 4-OH-BnzlHxy Bnzl 1.98 462 I IB-543 4-OH-Bnzl 4-F-Bnzl Bnzl 1.83 486 I IB-5444-OH-Bnzl Ph-Et i-Pnt 1.92 462 I IB-545 4-OH-Bnzl Cbm-E Bnzl 1.53 449 IIB-546 Ph-Et Bnzl Np-M 2.22 516 I IB-547 4-F-Bnzl Bnzl Ph-Et 2.15 484 IIB-548 4-F-Bnzl Cbm-E 4-OH-Bnzl 1.48 467 I IB-549 Hdr-E 4-F-Bnzl4-OH-Bnzl 1.51 440 I IB-550 i-Pnt Hxy Bnzl 2.22 426 I IB-551 i-Pnt Hxyi-Bu 2.24 392 I IB-552 i-Pnt 4-F-Bnzl Bnzl 2.11 450 I IB-553 i-Pnt4-F-Bnzl i-Bu 2.10 416 I IB-554 Ph-Et Hxy Bnzl 2.27 460 I IB-555 Ph-Et4-F-Bnzl Bnzl 2.13 484 I IB-556 Ph-Et 4-F-Bnzl i-Bu 2.12 450 I IB-557i-Pnt Hxy Ph-Et 2.31 440 I IB-558 i-Pnt Hxy Np-M 2.35 476 I IB-559 Ph-Et4-F-Bnzl i-Pnt 2.20 464 I IB-560 Chm 4-F-Bnzl Np-M 2.29 526 I IB-561Bnzl i-Pnt i-Bu 2.13 398 I IB-562 Bnzl Hxy Bnzl 2.20 446 I IB-563 BnzlHxy i-Bu 2.22 412 I IB-564 Bnzl 4-F-Bnzl Bnzl 2.08 470 I IB-565 Bnzl Hxyi-Pnt 2.27 426 I IB-566 Bnzl Hxy Ph-Et 2.24 460 I IB-567 Bnzl 4-F-Bnzli-Pnt 2.13 450 I IB-568 Bnzl 4-F-Bnzl Ph-Et 2.12 484 I IB-569 Bnzl Cbm-E4-OH-Bnzl 1.47 449 I IB-570 i-Bu Hxy i-Bu 2.22 378 I IB-571 i-Bu Hxyi-Pnt 2.31 392 I IB-572 i-Bu Hxy Ph-Et 2.25 426 I IB-573 i-Bu Hxy Np-M2.48 462 I IB-574 4-OH-Bnzl i-Pnt Bnzl 1.90 448 I IB-575 Cbx-E i-Bu Np-M1.80 450 I IB-576 i-Pnt 4-OH-Bnzl Ph-Et 1.97 462 I IB-577 i-Pnt4-OH-Bnzl Bnzl 1.87 448 I IB-578 Np-M Bnzl Np-M 2.24 552 I IB-579 Np-Mi-Pr Ph-Et 2.15 468 I IB-580 Np-M i-Pr Bnzl 2.05 454 I IB-581 Chm4-OH-Bnzl i-Bu 2.02 440 I IB-582 4-F-Bnzl 4-OH-Bnzl i-Pnt 1.96 466 IIB-583 4-F-Bnzl 4-OH-Bnzl Bnzl 1.88 486 I IB-584 Hdr-E Ph-Et Bnzl 1.75420 I IB-585 Hdr-E Np-M i-Bu 1.80 422 I IB-586 Hdr-E 4-F-Bnzl i-Bu 1.62390 I IB-587 i-Pnt Hdr-E 4-OH-Bnzl 1.36 402 I IB-588 Np-M Hdr-E Bnzl1.89 456 I IB-589 Np-M Np-M 4-OH-Bnzl 2.06 568 I IB-590 Np-M 4-F-Bnzli-Bu 2.16 486 I IB-591 Chm Hdr-E 4-OH-Bnzl 1.56 428 I IB-592 Chm4-F-Bnzl Bnzl 2.23 476 I IB-593 Ph-Et Hdr-E Np-M 1.88 470 I IB-594 Ph-Eti-Pnt Np-M 2.24 496 I IB-595 Ph-Et Hxy Np-M 2.33 510 I IB-596 Np-M Hdr-EPh-Et 1.94 470 I IB-597 Np-M Hxy Ph-Et 2.34 510 I IB-598 Np-M Hxy Np-M2.36 546 I IB-599 Np-M 4-F-Bnzl i-Pnt 2.26 500 I IB-600 Chm 4-F-Bnzli-Pnt 2.28 456 I IB-601 Bnzl Np-M 4-OH-Bnzl 1.98 518 I IB-602 Bnzl Hdr-ENp-M 1.85 456 I IB-603 Bnzl i-Pnt Np-M 2.29 482 I IB-604 Bnzl Hxy Np-M2.29 496 I IB-605 Bnzl i-Pr Np-M 2.11 454 I IB-606 Bnzl 4-OH-Bnzl Np-M1.96 518 I IB-607 i-Bu Hdr-E 4-OH-Bnzl 1.40 388 I IB-608 i-Bu 4-F-BnzlNp-M 2.15 486 I IB-609 i-Bu Cbm-E i-Bu 1.59 365 I IB-610 Hdr-E Cbx-ENp-M 1.56 438 I IB-611 i-Pnt Cbx-E i-Bu 1.68 380 I IB-612 Np-M Cbx-EBnzl 1.89 484 I IB-613 Chm Cbx-E i-Pnt 1.95 420 I IB-614 Chm Cbx-E Np-M2.02 490 I IB-615 4-F-Bnzl Cbx-E 4-OH-Bnzl 1.53 468 I IB-616 Bnzl Cbx-ENp-M 1.85 484 I IB-617 Hdr-E Bnzl i-Pnt 1.79 286 I IB-618 Hdr-E BnzlPh-Et 1.79 420 I IB-619 Hdr-E Bnzl Bnzl 1.71 406 I IB-620 Hdr-E i-BuPh-Et 1.74 386 I IB-621 Hdr-E i-Bu Np-M 1.80 422 I IB-622 Hdr-E i-BuBnzl 1.59 372 I IB-623 Hdr-E i-Bu 4-OH-Bnzl 1.48 388 I IB-624 i-Pnt BnzlPh-Et 2.17 446 I IB-625 Ph-Et i-Bu 4-OH-Bnzl 1.88 448 I IB-626 Chm Bnzli-Pnt 2.35 I IB-627 Chm Bnzl 4-OH-Bnzl 2.01 474 I IB-628 4-F-Bnzl Bnzl4-OH-Bnzl 1.94 486 I IB-629 4-F-Bnzl i-Bu Bnzl 2.06 436 I IB-6304-F-Bnzl i-Bu i-Bu 2.03 402 I IB-631 4-F-Bnzl i-Bu 4-OH-Bnzl 1.90 452 IIB-632 Bnzl Bnzl Ph-Et 2.12 466 I IB-633 i-Bu i-Bu Ph-Et 2.11 398 IIB-634 4-OH-Bnzl Bnzl Ph-Et 1.87 482 I IB-635 4-OH-Bnzl i-Bu Np-M 1.97484 I IB-636 i-Pnt Cbm-E Ph-Et 1.80 427 I IB-637 Chm Cbm-E Bnzl 1.83 439I IB-638 i-Pnt Hdr-E Bnzl 1.68 386 I IB-639 i-Pnt Hdr-E i-Bu 1.62 352 IIB-640 Ph-Et Hdr-E Bnzl 1.77 420 I IB-641 Ph-Et Hdr-E i-Bu 1.77 386 IIB-642 Ph-Et 4-F-Bnzl 4-OH-Bnzl 1.99 500 I IB-643 Np-M Hdr-E i-Bu 1.87422 I IB-644 Np-M i-Pnt i-Bu 2.27 448 I IB-645 Np-M i-Pnt 4-OH-Bnzl 2.06498 I IB-646 Chm Hdr-E i-Bu 1.79 378 I IB-647 Chm i-Pnt Bnzl 2.32 438 IIB-648 Chm i-Pnt 4-OH-Bnzl 2.07 454 I IB-649 4-F-Bnzl Hdr-E Bnzl 1.76424 I IB-650 4-F-Bnzl Hdr-E i-Bu 1.70 390 I IB-651 4-F-Bnzl i-Pnt Bnzl2.17 450 I IB-652 4-F-Bnzl i-Pnt i-Bu 2.14 416 I IB-653 4-F-Bnzl Np-Mi-Bu 2.19 486 I IB-654 4-F-Bnzl Hxy Bnzl 2.24 464 I IB-655 4-F-Bnzl Hxyi-Bu 2.24 I IB-656 4-F-Bnzl Hxy 4-OH-Bnzl 2.02 480 I IB-657 Hdr-E4-F-Bnzl i-Pnt 1.83 404 I IB-658 i-Pnt Hdr-E Ph-Et 1.79 400 I IB-659i-Pnt Hdr-E Np-M 1.94 436 I IB-660 Ph-Et Hxy i-Pnt 2.39 I IB-661 Np-MHdr-E i-Pnt 1.98 436 I IB-662 Np-M Hxy i-Pnt 2.44 I IB-663 Chm Hdr-EPh-Et 1.89 426 I IB-664 Chm Hdr-E Np-M 1.98 462 I IB-665 Chm Hxy Ph-Et2.50 I IB-666 Chm Hxy Np-M 2.54 I IB-667 Chm 4-F-Bnzl Ph-Et 2.31 490 IIB-668 4-F-Bnzl Hdr-E i-Pnt 1.77 404 I IB-669 4-F-Bnzl Hdr-E Ph-Et 1.78438 I IB-670 4-F-Bnzl Hdr-E Np-M 1.87 474 I IB-671 4-F-Bnzl i-Pnt Ph-Et2.21 464 I IB-672 4-F-Bnzl i-Pnt Np-M 2.27 500 I IB-673 4-F-Bnzl Hxyi-Pnt 2.30 I IB-674 4-F-Bnzl Hxy Ph-Et 2.31 I IB-675 4-F-Bnzl Hxy Np-M2.37 I IB-676 Bnzl Hdr-E Bnzl 1.70 406 I IB-677 Bnzl Hdr-E i-Bu 1.66 372I IB-678 Bnzl i-Pnt 4-OH-Bnzl 1.95 448 I IB-679 Bnzl Hxy 4-OH-Bnzl 2.02462 I IB-680 Bnzl Hdr-E i-Pnt 1.79 386 I IB-681 Bnzl Hdr-E Ph-Et 1.76420 I IB-682 i-Bu Hdr-E i-Bu 1.62 338 I IB-683 i-Bu i-Pnt i-Bu 2.11 364I IB-684 i-Bu i-Pnt 4-OH-Bnzl 1.88 414 I IB-685 i-Bu Hdr-E i-Pnt 1.71352 I IB-686 i-Bu Hdr-E Ph-Et 1.74 386 I IB-687 i-Bu Hdr-E Np-M 1.82 422I IB-688 i-Bu i-Pnt Ph-Et 2.17 412 I IB-689 i-Bu 4-F-Bnzl i-Pnt 2.13 416I IB-690 i-Bu 4-F-Bnzl Ph-Et 2.22 I IB-691 Ph-Et Bnzl Cbx-E 1.84 448 IIB-692 4-F-Bnzl Bnzl Cbx-E 1.79 452 I IB-693 Np-M i-Pnt Cbx-E 1.99 464 IIB-694 Cbx-E Bnzl i-Pnt 1.79 414 I IB-695 Cbx-E Bnzl i-Bu 1.64 400 IIB-696 Cbx-E i-Bu i-Pnt 1.77 380 I IB-697 Bnzl i-Pnt Cbx-E 1.84 414 IIB-698 Bnzl Bnzl Cbx-E 1.82 434 I IB-699 Bnzl i-Bu Cbx-E 1.74 400 IIB-700 i-Bu i-Pnt Cbx-E 1.81 380 I IB-701 Hdr-E Cbm-E Ph-Et 1.46 401 IIB-702 Hdr-E Cbm-E Bnzl 1.39 387 I IB-703 i-Pnt Cbm-E Np-M 1.86 463 IIB-704 i-Pnt Cbm-E Bnzl 1.71 413 I IB-705 i-Pnt Cbm-E i-Bu 1.71 379 IIB-706 i-Pnt Cbm-E 4-OH-Bnzl 1.38 429 I IB-707 Ph-Et Cbm-E Bnzl 1.77 447I IB-708 Ph-Et Cbm-E i-Bu 1.77 413 I IB-709 Ph-Et Cbm-E 4-OH-Bnzl 1.55463 I IB-710 Chm Cbm-E Ph-Et 1.91 453 I IB-711 Chm Cbm-E i-Bu 1.84 405 IIB-712 4-F-Bnzl Cbm-E Bnzl 1.76 451 I IB-713 4-F-Bnzl Cbm-E i-Bu 1.71417 I IB-714 Hdr-E i-Pnt Bnzl 1.72 386 I IB-715 Hdr-E i-Pnt i-Bu 1.71352 I IB-716 Hdr-E i-Pnt 4-OH-Bnzl 1.61 402 I IB-717 Hdr-E Ph-Et i-Bu1.74 386 I IB-718 i-Pnt Np-M i-Bu 2.29 448 I IB-719 i-Pnt Np-M 4-OH-Bnzl2.02 498 I IB-720 Ph-Et i-Pnt 4-OH-Bnzl 1.99 462 I IB-721 Np-M Ph-Et4-OH-Bnzl 2.09 532 I IB-722 Chm Ph-Et i-Bu 2.32 438 I IB-723 Chm Np-M4-OH-Bnzl 2.13 524 I IB-724 4-F-Bnzl i-Pnt 4-OH-Bnzl 2.00 466 I IB-7254-F-Bnzl Ph-Et i-Bu 2.16 450 I IB-726 4-F-Bnzl Ph-Et 4-OH-Bnzl 1.96 500I IB-727 Hdr-E i-Pnt Np-M 1.88 436 I IB-728 Np-M i-Pnt Ph-Et 2.33 496 IIB-729 Np-M Ph-Et Np-M 2.38 I IB-730 Chm i-Pnt Ph-Et 2.36 I IB-731 ChmNp-M i-Pnt 2.46 I IB-732 4-F-Bnzl Ph-Et i-Pnt 2.22 464 I IB-733 Bnzli-Pnt Ph-Et 2.20 446 I IB-734 Bnzl Cbm-E Bnzl 1.74 433 I IB-735 i-BuNp-M i-Bu 2.25 434 I IB-736 i-Bu i-Pnt Np-M 2.27 448 I IB-737 i-Bu Cbm-ENp-M 1.84 449 I IB-738 i-Bu Cbm-E 4-OH-Bnzl 1.40 415 I IB-739 4-OH-Bnzli-Pnt i-Bu 1.84 414 I IB-740 4-OH-Bnzl i-Pnt Ph-Et 1.95 462 I IB-7414-OH-Bnzl i-Pnt Np-M 2.01 498 I IB-742 4-OH-Bnzl Cbm-E Ph-Et 1.59 463 IIB-743 4-OH-Bnzl Cbm-E Np-M 1.75 499 I IB-744 Hdr-E Bnzl i-Bu 1.67 372 IIB-745 Hdr-E Bnzl 4-OH-Bnzl 1.51 422 I IB-746 Hdr-E i-Bu i-Bu 1.57 338 IIB-747 i-Pnt Bnzl Np-M 2.21 482 I IB-748 i-Pnt Bnzl i-Bu 2.10 398 IIB-749 i-Pnt Bnzl 4-OH-Bnzl 1.82 448 I IB-750 i-Pnt i-Bu Ph-Et 2.16 412I IB-751 i-Pnt i-Bu Np-M 2.18 448 I IB-752 i-Pnt i-Bu Bnzl 2.06 398 IIB-753 i-Pnt i-Bu i-Bu 2.04 364 I IB-754 i-Pnt i-Bu 4-OH-Bnzl 2.34 IIB-755 Ph-Et Bnzl i-Pnt 2.22 446 I IB-756 Ph-Et Bnzl Bnzl 2.10 466 IIB-757 Ph-Et Bnzl i-Bu 2.13 432 I IB-758 Ph-Et Bnzl 4-OH-Bnzl 1.90 482 IIB-759 Ph-Et i-Bu Bnzl 2.08 432 I IB-760 Ph-Et i-Bu i-Bu 2.10 398 IIB-761 Np-M Bnzl i-Bu 2.22 468 I IB-762 Np-M i-Bu i-Bu 2.16 434 I IB-763Np-M i-Bu 4-OH-Bnzl 1.97 484 I IB-764 Chm Bnzl Ph-Et 2.31 472 I IB-765Chm Bnzl i-Bu 2.24 424 I IB-766 Chm i-Bu Ph-Et 2.27 438 I IB-767 Chmi-Bu Np-M 2.32 474 I IB-768 Chm i-Bu Bnzl 2.19 424 I IB-769 Chm i-Bui-Bu 2.22 390 I IB-770 Chm i-Bu 4-OH-Bnzl 1.99 440 I IB-771 4-F-BnzlBnzl i-Pnt 2.18 450 I IB-772 4-F-Bnzl Bnzl Bnzl 2.10 470 I IB-7734-F-Bnzl Bnzl i-Bu 2.12 436 I IB-774 4-F-Bnzl i-Bu Ph-Et 2.11 450 IIB-775 Ph-Et i-Pnt Bnzl 2.18 446 I IB-776 Bnzl i-Pnt Bnzl 2.13 432 IIB-777 Bnzl Bnzl Np-M 2.20 502 I IB-778 Bnzl i-Bu Ph-Et 2.14 432 IIB-779 Bnzl i-Bu 4-OH-Bnzl 1.85 434 I IB-780 i-Bu i-Pnt Bnzl 2.15 398 IIB-781 i-Bu Bnzl i-Pnt 2.19 398 I IB-782 i-Bu Bnzl Np-M 2.16 468 IIB-783 i-Bu Bnzl 4-OH-Bnzl 1.85 434 I IB-784 i-Bu i-Bu Np-M 2.19 434 IIB-785 i-Bu i-Bu 4-OH-Bnzl 1.81 400 I IB-786 4-OH-Bnzl Bnzl i-Pnt 1.90448 I IB-787 4-OH-Bnzl Bnzl i-Bu 1.80 434 I IB-788 Ph-Et Cbm-E Np-M 1.91497 I IB-789 Ph-Et i-Pr Np-M 2.19 468 I IB-790 Np-M Cbm-E Bnzl 1.88 483I IB-791 i-Pnt Np-M Bnzl 2.27 483 I IB-792 Ph-Et Np-M i-Bu 2.29 482 IIB-793 Ph-Et Np-M 4-OH-Bnzl 2.09 532 I IB-794 Np-M i-Pnt Bnzl 2.29 482 IIB-795 Np-M Ph-Et Bnzl 2.32 516 I IB-796 Np-M Np-M i-Bu 2.37 518 IIB-797 Np-M 4-F-Bnzl Bnzl 2.24 520 I IB-798 Chm Np-M Bnzl 2.41 508 IIB-799 4-F-Bnzl Np-M Bnzl 2.25 520 I IB-800 Ph-Et Np-M i-Pnt 2.36 497 IIB-801 Ph-Et 4-F-Bnzl Np-M 2.27 534 I IB-802 Np-M i-Pnt Np-M 2.42 532 IIB-803 Np-M Np-M i-Pnt 2.41 532 I IB-804 Np-M Np-M Ph-Et 2.39 566 IIB-805 Np-M 4-F-Bnzl Ph-Et 2.28 534 I IB-806 Np-M 4-F-Bnzl Np-M 2.36 570I IB-807 Chm Np-M Ph-Et 2.47 522 I IB-808 Chm Np-M Np-M 2.47 558 IIB-809 4-F-Bnzl Np-M Ph-Et 2.28 534 I IB-810 4-F-Bnzl Np-M Np-M 2.31 570I IB-811 Bnzl Np-M i-Pnt 2.30 482 I IB-812 Bnzl 4-F-Bnzl Np-M 2.21 520 IIB-813 Bnzl Cbm-E Np-M 1.86 483 I IB-814 i-Bu Np-M Np-M 2.39 518 IIB-815 4-OH-Bnzl Np-M Bnzl 2.01 518 I IB-816 4-OH-Bnzl Np-M Ph-Et 2.05532 I IB-817 Np-M Bnzl Ph-Et 2.32 516 I IB-818 Np-M Cbm-E Np-M 2.00 533I IB-819 Chm Bnzl Np-M 2.40 508 I IB-820 Hdr-E Np-M Bnzl 1.89 456 IIB-821 i-Pnt Ph-Et 4-OH-Bnzl 1.94 462 I IB-822 Ph-Et i-Pnt i-Bu 2.13 412I IB-823 Ph-Et Np-M Bnzl 2.33 516 I IB-824 Ph-Et Hxy i-Bu 2.35 426 IIB-825 Np-M Np-M Bnzl 2.39 552 I IB-826 Chm Ph-Et 4-OH-Bnzl 2.02 488 IIB-827 Hdr-E i-Pnt Ph-Et 1.82 400 I IB-828 Hdr-E Np-M i-Pnt 1.98 436 IIB-829 Hdr-E Np-M Ph-Et 1.99 470 I IB-830 Hdr-E Np-M Np-M 2.02 506 IIB-831 Hdr-E 4-F-Bnzl Np-M 1.90 474 I IB-832 i-Pnt Np-M Ph-Et 2.45 496 IIB-833 i-Pnt Np-M Np-M 2.45 532 I IB-834 i-Pnt 4-F-Bnzl Np-M 2.24 500 IIB-835 Chm i-Pnt Np-M 2.46 488 I IB-836 Bnzl Ph-Et 4-OH-Bnzl 1.98 482 IIB-837 Bnzl Np-M Bnzl 2.30 502 I IB-838 Bnzl Ph-Et Np-M 2.28 516 IIB-839 i-Bu Hxy Bnzl 2.24 412 I IB-840 i-Bu 4-F-Bnzl Bnzl 2.11 436 IIB-841 4-OH-Bnzl Hdr-E Np-M 1.72 472 I IB-842 4-OH-Bnzl Np-M Np-M 2.08568 I IB-843 4-OH-Bnzl i-Bu Ph-Et 1.89 448 I IB-844 Ph-Et Cbx-E i-Bu0.85 414 C IB-845 Ph-Et Cbx-E i-Pnt 0.89 428 C IB-846 4-OH-Bnzl Cbx-Ei-Pnt 0.73 430 C IB-847 4-OH-Bnzl Cbx-E Bnzl 0.75 450 C IB-848 4-OH-BnzlCbx-E Ph-Et 0.74 C IB-849 Bnzl Cbx-E i-Bu 0.80 400 C IB-850 Bnzl Cbx-Ei-Pnt 0.84 414 C IB-851 Bnzl Cbx-E Ph-Et 0.85 448 C IB-852 i-Bu Cbx-EPh-Et 0.84 414 C IB-853 i-Bu Cbx-E 4-OH-Bnzl 0.54 416 C IB-854 i-PntCbx-E Ph-Et 0.84 428 C IB-855 i-Pnt Cbx-E 4-OH-Bnzl 0.68 430 C IB-856Chm Cbx-E Ph-Et 0.91 454 C IB-857 Chm Cbx-E 4-OH-Bnzl 0.77 456 C IB-858i-Pnt Cbx-E Bnzl 0.80 414 C IB-859 Chm Cbx-E Bnzl 0.90 440 C IB-8604-OH-Bnzl Cbx-E i-Bu 0.69 416 c

Measure- Reten- ment Compound tion Mass condi- number R₁ R₂ R₃ R₄ RT(min) (M + H)⁺ tion IB-861 methyl 2-(1H-in- benzyl H 1.212 429 Bdol-3-yl) ethyl IB-862 benzyl Np-M i-Bu H 1.29 468 B IB-863 benzyl4-(tri- i-Bu H 1.298 486 B fluorometh- yl)benzyl IB-864 4-Cl-Bnzl benzyli-Bu H 1.288 452 B IB-865 3-Cl-Bnzl benzyl i-Bu H 1.293 452 B IB-8664-methoxy- benzyl i-Bu H 1.263 448 B benzyl IB-867 4-methyl benzyl i-BuH 1.288 432 B benzyl IB-868 i-Pnt 1-Bu benzyl H 1.277 398 B IB-869 i-Bu1-Bu 4-Cl-Bnzl H 1.275 418 B IB-870 i-Bu 1-Pnt benzyl H 1.287 398 BIB-871 i-Bu 4-Cl-Bnzl i-Bu H 1.285 418 B IB-872 4-hydroxy- benzyl i-Bu H1.187 434 B benzyl IB-873 4-(dimethyl- benzyl i-Bu H 1.255 461 B amino)benzyl IB-874 4-(tert- benzyl i-Bu H 1.345 474 B butyl) benzyl IB-875i-Bu benzyl i-Pnt H 1.283 398 B IB-876 i-Pnt benzyl i-Bu H 1.067 398 BIB-877 4-(tri- benzyl i-Bu H 1.29 502 B fluorometh- yl)benzyl IB-8784-ethoxy benzyl i-Bu H 1.275 462 B benzyl IB-879 benzyl naphthalen- i-BuH 1.282 468 B 2-yl- methyl IB-880 4-methyl benzyl i-Bu ethyl 1.332 460 Bbenzyl IB-881 4-methyl benzyl i-Bu i-Bu 1.495 488 B benzyl IB-8824-methyl benzyl i-Bu acetyl 1.223 474 B benzyl IB-883 4-methyl benzyli-Bu 3-methyl- 1.312 516 B benzyl butanoyl IB-884 4-methyl benzyl i-Bu2-phenyl- 1.3 550 B benzyl acetyl IB-885 4-methyl benzyl i-Bu methoxy-1.267 490 B benzyl carbonyl IB-886 4-methyl benzyl i-Bu 2-methyl- 1.328532 B benzyl propoxy carbonyl IB-887 4-methyl benzyl i-Bu benzyloxy-1.347 566 B benzyl carbonyl IB-888 4-methyl benzyl i-Bu amino- 1.173 475B benzyl carbonyl IB-889 4-methyl benzyl i-Bu N-benzyl- 1.288 565 Bbenzyl amino- carbonyl IB-890 benzyl pyridin- i-Bu H 1.11 419 B4-ylmethyl IB-891 4-(dimethyl- 3-hydroxy- i-Bu H 1.223 477 B amino)-benzyl benzyl IB-892 4-(dimethyl- 4-hydroxy i-Bu H 1.208 477 B amino)-benzyl benzyl IB-893 4-methoxy- benzyl benzyl H 0.98 482 C benzyl IB-8944-methoxy- benzyl benzyl tert-butoxy- 1.06 582 C benzyl carbonyl IB-895methyl benzyl benzyl tert-butoxy- 0.97 476 C carbonyl IB-896 methylbenzyl benzyl H 0.84 376 C IB-897 phenethyl benzyl 2-(tert-butyl- H 1.13534 C dimethyl- silyloxy) ethyl IB-898 cyclopentyl- 4-(tert-2-(tert-butoxy- H 1.16 554 C methyl butoxy)- carbon- benzyl yl)ethylIB-899 cyclopentyl- 4-(tert- 2-(tert- methoxy- 1.04 612 C methyl butoxy)butoxy- carbonyl benzyl carbonyl)ethyl IB-900 cyclopentyl- 4-hydroxy-2-carboxy- H 0.77 442 C methyl benzyl ethyl IB-901 cyclopentyl-4-hydroxy- 2-carboxy- methoxy- 0.76 500 C methyl benzyl ethyl carbonylIB-902 4-nitro- 4-(tert- 2-(tert-bu- H 1.06 607 C benzyl butoxy)benzyltoxycarbon- yl)ethyl IB-903 phenethyl benzyl 2-hydroxy- H 0.85 420 Cethyl IB-904 phenethyl benzyl 2-hydroxy- acetyl 0.81 462 C ethyl IB-905phenethyl benzyl 2-hydroxy- methoxy- 0.86 478 C ethyl carbonyl IB-906phenethyl benzyl 2-hydroxy- ethyl 0.9 448 C ethyl IB-907 4-nitro-4-(tert- 2-(tert-bu- methoxy- 1.04 665 C benzyl butoxy)benzyltoxycarbon- carbonyl yl)ethyl IB-908 1-naphthyl- benzyl benzyl benzyl1.14 592 C methyl IB-909 4-amino- 4-(tert- 2-(tert-bu- methoxy- 0.94 635C benzyl butoxy)benzyl toxycarbon- carbonyl yl)ethyl IB-910 4-(cyclo-4-(tert- 2-(tert-bu- methoxy- 1.05 731 C pentyl- butoxy)benzyltoxycarbon- carbonyl carbonyl- yl)ethyl amino) benzyl IB-911 4-(2-car-4-(tert- 2-(tert-bu- methoxy- 0.92 735 C boxyethyl- butoxy)benzyltoxycarbon- carbonyl carbonyl- yl)ethyl amino) benzyl IB-912 4-(2-carba-4-(tert- 2-(tert-bu- methoxy- 0.9 734 C moylethyl- butoxy)benzyltoxycarbon- carbonyl carbonyl- yl)ethyl amino) benzyl IB-913 4-nitro-4-hydroxy- 2-carboxyl H 0.76 495 C benzyl benzyl ethyl IB-914 4-(cyclo-4-hydroxy- 2-carboxyl methoxy- 0.79 619 C pentyl- benzyl ethyl carbonylcarbonyl- amino) benzyl IB-915 4-nitro- 4-(tert- 2-(tert-bu-tert-butoxy- 1.12 707 C benzyl butoxy)benzyl toxycarbon- carbonylyl)ethyl IB-916 4-(cyclo- 4-(tert- 2-(tert-bu- methoxy- 1.14 717 Cmethyl- butoxy)benzyl toxycarbon- carbonyl carbonyl- yl)ethyl amino)benzyl IB-917 4-(cyclo- 4-(tert- 2-(tert-bu- tert-butoxy- 1.14 774 Cpentyl- butoxy)benzyl toxycarbon- carbonyl carbonyl- yl)ethyl amino)benzyl IB-918 4-(cyclo- 4-(tert- 2-(tert-bu- tert-butoxy- 1.24 760 Cmethyl- butoxy)benzyl toxycarbon- carbonyl carbonyl- yl)ethyl amino)benzyl IB-919 4-nitro- 4-(tert- 2-(tert-bu- formyl 0.98 635 C benzylbutoxy)benzyl toxycarbon- yl)ethyl IB-920 4-(2-carba- 4-hydroxy-2-carboxyl methoxy- 0.61 622 C moylethyl- benzyl ethyl carbonylcarbonyl- amino) benzyl IB-921 4-(cyclo- 4-hydroxy- 2-carboxyl methoxy-0.82 605 C pentyl- benzyl ethyl carbonyl methyl- amino) benzyl IB-9224-(cyclo- 4-hydroxy- 2-carboxyl H 0.79 561 C pentyl- benzyl ethylcarbonyl- amino) benzyl IB-923 4-(cyclo- 4-hydroxy- 2-carboxyl H 0.75547 C pentyl- benzyl ethyl methyl- amino) benzyl Formula XXIB

Measure- Reten- ment Compound tion Mass condi- number R₁ R_(2A) R_(2B)R₃ R₄ RT (min) (M + H)⁺ tion IB- 4-Me- H Bnzl i-Bu N- 2.88 531 B1 924Bnzl isobutyl- amino carbonyl IB- i-Bu H 4-Cl-Bnzl Ph-Et H 2.93 466 B1925 IB- i-Bu H 3-Cl-Bnzl Ph-Et H 2.94 466 B1 926 IB- i-Bu H 4-MeO-BnzlPh-Et H 2.84 462 B1 927 IB- i-Bu H 4-Me-Bnzl Ph-Et H 2.93 446 B1 928 IB-i-Bu H 2-Npm Ph-Et H 2.97 482 B1 929 IB- i-Bu H Bnzl Ph-Pr H 1.36 446 B930 IB- i-Bu H 3-Cl-Bnzl Ph-Pr H 1.31 480 B 931 IB- i-Bu H 3-F-BnzlPh-Pr H 1.35 464 B 932 IB- i-Bu H 3-Me-Bnzl Ph-Pr H 1.38 460 B 933 IB-i-Bu H 3-MeO-Bnzl Ph-Pr H 1.36 476 B 934 IB- i-Bu H 3-Cl-Bnzl Ph-Bu H1.33 494 B 935 IB- i-Bu H 3-F-Bnzl Ph-Bu H 1.29 478 B 936 IB- i-Bu H3-Me-Bnzl Ph-Bu H 1.38 474 B 937 IB- i-Bu H 3-MeO-Bnzl Ph-Bu H 1.31 491B 938 IB- i-Bu H Bnzl Ph-Bu H 1.32 461 B 939 IB- i-Pnt H 3-F-Bnzl Ph-PrH 1.31 478 B 940 IB- 1-Npm H pentyl Ph-Et H 1.08 496 C 941 IB- 1-Npm Hcyclohexyl Ph-Et H 1.08 508 C 942 IB- 1-Npm H cyclopentyl Ph-Et H 1.06494 C 943 IB- 1-Npm piperidine† Ph-Et H 1.04 494 C 944 IB- 1-Npmpyrrolidine† Ph-Et H 1.00 480 C 945 IB- 1-Npm H Hxy 4- H 1.14 524 C 946methyl- phen- ethyl IB- 1-Npm H Hxy 2- H 1.16 560 C 947 (naph- thalen-2- yl)ethyl IB- 1-Npm H heptyl Ph-Et H 1.14 524 C 948 IB- 1-Npm H Hxy 4-H 1.19 552 C 949 isopropyl- phen- ethyl IB- 1-Npm H Hxy cyclo H 1.19 516C 950 hexyl ethyl IB- tBuO- H 4-fluoro 1-Npm H 1.06 544 C 951 Ephenethyl IB- H H 4-tBuO-Bnzl tBOC- methoxycar- 0.93 530 C 952 E bonylIB- 2- H 4-tBuO-Bnzl tBOC- methoxycar- 1.17, 648 C 953** phenyl E bonyl1.20 acetyl IB- 3- H 4-tBuO- tBOC- methoxycar- 1.16, 614 C 954** methylBnzl E bonyl 1.21 buta- noyl IB- 2- H 4-OH-Bnzl Cbx-E methoxycar- 0.78,536 C 955** phenyl- bonyl 0.83 acetyl IB- 3- H 4-OH-Bnzl Cbx-Emethoxycar- 0.75, 502 C 956** methyl- bonyl 0.81 buta- noyl IB- i-Bu HPh-Et Ph-Et H 2.89 446 B1 957 IB- i-Bu H 1-Npm Ph-Et H 2.97 482 B1 958IB- Chm H tBuO-E 1-Npm H 1.10 518 C 959 IB- tBuO- H Ph-Et 1-Npm H 1.06526 C 960 E IB- Hdr-E H 4- 1-Npm H 0.90 488.3 C 961 fluorophen ethyl IB-3- H 4-F-Bnzl 1-Npm H 1.04 544.4 C 962 tert- butoxy- propyl IB- tBuO- H4-Cl-Bnzl 1-Npm H 1.07, 546.3 C 963 E 1.09 IB- Hdr-E H 4-Cl-Bnzl 1-Npm H0.92 490.3 C 964 IB- Hdr-E H 4-Cl-Bnzl 1-Npm H 0.92 490.2 C 965 IB- 3- H4-F-Bnzl 1-Npm H 0.87 488.3 C 966 hydroxy- propyl IB- 1-Npm H Hxy 3- H1.14 524.4 C 967 methyl- phen ethyl IB- 1-Npm H β- Ph-Et H 1.01 546.4 C968 hydroxyphen- ethyl IB- 1-Npm H α- Ph-Et H 1.01 560.4 C 969hydroxymethyl- phen- ethyl IB- 1-Npm H α- Ph-Et H 1.03 560.4 C 970hydroxymethyl- phenethyl IB- 4-Nt- H Bnzl tBOC- H 0.97 535 C 971 Bnzl EIB- 4-Nt- H Bnzl tBOC- ethoxycar- 0.98 563 C 972 Bnzl E bonyl IB- H HBnzl tBOC- ethoxycar- 0.87 472 C 973 E bonyl IB- phenyl- H Bnzl tBOC-ethoxycar- 0.14, 590 C 974 acetyl E bonyl 0.16 IB- phenyl- H Bnzl Cbx-Eethoxycar- 0.91, 534 C 975 acetyl bonyl 0.97 IB- 4- H Bnzl tBOC-ethoxycar- 0.87 577 C 976 amino E bonyl benzyl IB- 4- H Bnzl tBOC-ethoxycar- 1.09 659 C 977 (cyclo- E bonyl pentyl- methyl- amino) benzylIB- 4- H Bnzl Cbx-E ethoxycar- 0.93 603 C 978 (cyclo- bonyl pentyl-methyl- amino) benzyl IB- 4- H Bnzl tBOC- ethoxycar- 1.00 673 C 979(cyclo- E bonyl pentyl carbonyl amino) benzyl IB- 3- H Bnzl tBOC-ethoxycar- 1.13, 556 C 980** methyl- E bonyl 1.16 buta- noyl IB- H HBnzl Bnzl tert- 0.93 462 C 981 butoxycar- bonyl IB- 3- H Bnzl Cbx-Eethoxycar- 0.89, 500 C 982** methyl- bonyl 0.96 buta- noyl IB- isopro- HBnzl Cbx-E ethoxycar- 0.94 502 C 983 poxy bonyl carbonyl IB- phenyl- HBnzl 3- ethoxycar- 1.05, 562 C 984** acetyl ethoxy- bonyl 1.08 3- oxo-propyl IB- benzoyl H Bnzl Bnzl tert- 1.22 566 C 985 butoxycar- bonyl IB-phenyl- H Bnzl Bnzl tert- 1.23 580 C 986 acetyl butoxycar- bonyl IB- 4-H Bnzl Cbx-E ethoxycar- 0.87 617 C 987 (cyclo- bonyl pentyl- carbonylamino) benzyl IB- 1-Npm H 4-F-Bnzl 2-OH- H 0.89 474.3 C 988 Et IB- 2-OH-H Ph-Et 1-Npm H 0.89 470.3 C 989 Et IB- 4- H Bnzl i-Bu H 1.02 490.3 C990 tBuO- Bnzl IB- 4- H i-Bu Bnzl H 1.03 490.4 C 991 tBuO- Bnzl IB- 2- HBnzl 1-Npm H 1.04 512.4 C 992 OtBu-Et IB- 2-OH- H Bnzl 1-Npm H 0.87456.3 C 993 Et IB- 4-OH- H i-Bu Bnzl H 0.85 434.3 C 994 Bnzl IB- 1-Npm H4-F-Bnzl 2- H 1.17 588.4 C 995 OTBS- Et †Ring formed together by R_(2A)and R_(2B) **IB-953, 954, 955, 956, 980, 982, and 984 are mixtures ofcis-trans isomers. For this reason, two values are shown for theretention of LCMS.

TABLE 4

Compound Synthesis Number R₁ R₂ R₃ R₄ method Intermediate IF-1  i-BuBnzl Bnzl H EX IIF-1  IF-2  i-Bu i-Bu i-Bu H IF-1  IIF-2  IF-3  i-Bui-Bu Bnzl H IF-1  IIF-3  IF-4  Bnzl i-Bu i-Bu H IF-1  IIF-4  IF-5  i-BuBnzl i-Bu H IF-1  IIF-5  IF-6  Bnzl i-Bu Bnzl H IF-1  IIF-6  IF-7  BnzlBnzl i-Bu H IF-1  IIF-7  IF-8  Bnzl Bnzl Bnzl H IF-1  IIF-8  IF-9  i-PntBnzl Bnzl H IF-1  IIF-9  IF-10 Bnzl Bnzl i-Pnt H IF-1  IIF-10 IF-11 i-BuBnzl Ph-Et H IF-1  IIF-11 IF-12 i-Bu Ph-Et Bnzl H IF-1  IIF-12 IF-13i-Bu Bnzl 3-Me-Bnzl H IF-1  IIF-13 IF-14 i-Bu Bnzl 4-Me-Bnzl H IF-1 IIF-14 IF-15 i-Bu 3-Me-Bnzl Bnzl H IF-1  IIF-15 IF-16 i-Bu 4-Me-BnzlBnzl H IF-1  IIF-16 IF-17 i-Bu 3-Cl-Bnzl Bnzl H IF-1  IIF-17 IF-18 i-Bu4-Cl-Bnzl Bnzl H IF-1  IIF-18 IF-19 3,4-Cl₂-Bnzl Bnzl i-Bu H IF-1 IIF-19 IF-20 Bnzl 3,4-Cl₂-Bnzl i-Bu H IF-1  IIF-20 IF-22 i-Bu 4-OH-BnzlBnzl H IF-40 IF-23 IF-23 i-Bu 4-(tert- Bnzl H IF-1  IIF-23 butoxy)benzylIF-24 i-Bu Np-M Bnzl H IF-1  IIF-24 IF-25 i-Bu Hdr-E Bnzl H IF-1  IIF-25IF-26 i-Bu Cbx-E Bnzl H EX IF-27 IF-27 i-Bu 2-(tert-butoxy)- Bnzl HIF-1  IIF-27 2-oxoethyl IF-28 i-Bu Cbm-E Bnzl H IF-1  IIF-28 IF-29 i-Bu4-aminobutyl Bnzl H IB-29 IF-30 IF-30 i-Bu 4-((tert- Bnzl H IF-1  IIF-30butoxycarbonyl) amino)butyl IF-31 i-Bu Chm Bnzl H IF-1  IIF-31 IF-32i-Bu (tetrahydro-2H- Bnzl H IF-1  IIF-32 pyran-2- yl)methyl IF-33 i-BuBnzl 4-aminobutyl H EX IF-34 IF-34 i-Bu Bnzl 4-((tert- H IF-1  IIF-34butoxycarbonyl) amino)butyl IF-35 i-Bu Bnzl Cbx-E H IB-35 IF-73 IF-36i-Bu Bnzl 3-methoxy-3- H IF-1  IIF-36 oxopropyl IF-38 i-Bu Bnzl Chm HIF-1  IIF-38 IF-39 Chm Bnzl Bnzl H IF-1  IIF-39 IF-40 4-OH-Bnzl BnzlBnzl H EX IF-41 IF-41 4-(tert- Bnzl Bnzl H EX IIF-41 butoxy)benzyl IF-42Np-M Bnzl Bnzl H IF-1  IIF-42 IF-43 i-Bu Bnzl Bnzl Ac EX IF-1  IF-44i-Bu i-Bu i-Bu Ac IF-43 IF-2  IF-45 i-Bu i-Bu Bnzl Ac IF-43 IF-3  IF-46Bnzl i-Bu i-Bu Ac IF-43 IF-4  IF-47 i-Bu Bnzl i-Bu Ac IF-43 IF-5  IF-49Bnzl Bnzl i-Bu Ac IF-43 IF-7  IF-50 Bnzl Bnzl Bnzl Ac IF-43 IF-8  IF-54i-Bu Ph-Et Bnzl Ac IF-43 IF-12 IF-57 i-Bu 3-Me-Bnzl Bnzl Ac IF-43 IF-15IF-58 i-Bu 4-Me-Bnzl Bnzl Ac IF-43 IF-16 IF-68 i-Bu Bnzl Bnzl Bz IB-68IF-1  IF-69 i-Bu Bnzl Bnzl Et IB-69 IF-1  IF-70 i-Bu Bnzl Bnzl methoxy-IB-70 IF-1  carbonyl IF-71 i-Bu Bnzl Bnzl Me EX IF-1  IF-72 Bnzl Bnzli-Bu Et IB-69 IF-7  IF-73 i-Bu Bnzl Cbx-E tBOC IB-73 IF-74 IF-74 i-BuBnzl 3-methoxy-3- tBOC IB-74 IF-36 oxopropyl IF-76 3-(tert-butoxy)- BnzlBnzl H IF-1  IIF-76 3-oxopropyl IF-77 Bnzl Bnzl 4-OH-Bnzl H IF-1  IIF-77IF-80 Np-M Bnzl Pr H IB-1  IIF-80 Com- LCMS pound t_(R) Mass ElutionYield number Name of compound (min) (M + H)⁺ condition (%) IF-1 (3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1- 0.99 418 B  62isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-2  (3S*,3aS*,6S*,7R*,7aS*)-N,1,7-triisobutyloctahydro- 0.93 350 B  736H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-3 (3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N,1- 0.96 384 B  67diisobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-4  (3S*,3aS*,6S*,7R*,7aS*)-1-benzyl-N,7- 0.97 384 B  82diisobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-5  (3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1,7- 0.95 384 B  73diisobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-6  (3S*,3aS*,6S*,7R*,7aS*)-1,7-dibenzyl-N- 1.00 418 B  68isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-7  (3S*,3aS*,6S*,7R*,7aS*)-N,1-dibenzyl-7- 0.99 418 B  64isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-8  (3S*,3aS*,6S*,7R*,7aS*)-N,1,7-tribenzyloctahydro- 1.02 452 B  696H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-9 (3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1- 1.01 432 B  47isopentyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-10 (3S*,3aS*,6S*,7R*,7aS*)-N,1-dibenzyl-7- 1.02 432 B  60isopentyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-11 (3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7- 0.99 432 B  63phenethyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-12 (3S*,3aS*,6S*,7R*,7aS*)-1-benzyl-7-isobutyl-N- 1.01 432 B  60phenethyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-13 (3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3- 1.01 432 B  55methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-14(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(4- 1.01 432 B  57methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-15(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(3- 1.02 432 B  62methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-16(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(4- 1.02 432 B  63methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-17 (3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N-(3-1.03 452 B  69 chlorobenzyl)-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-18(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N-(4- 1.03 452 B  68chlorobenzyl)-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-19(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-(3,4- 1.13 486 B  38dichlorobenzyl)-7-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-20(3S*,3aS*,6S*,7R*,7aS*)-1-benzyl-N-(3,4- 1.06 486 B  37dichlorobenzyl)-7-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-22(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N-(4- 0.71 434 A  95hydroxybenzyl)-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-23(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(4- 0.87 490 A  95(tert-butoxy)benzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-24(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N- 0.85 468 A  77(naphthalen-1-ylmethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-25(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N-(2- 0.65 372 A  95hydroxyethyl)-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-263-((3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1- 0.66 400 A 100isobutyloctahydro-1H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide)propanoic acid IF-27(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(2- 0.81 456 A 100(tert-butoxy)-2-oxoethyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-28(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N-(3-amino-3- 0.67 399 A  53oxopropyl)-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-29(3S*,3aS*,6S*,7R*,7aS*)-N-(4-aminobutyl)-7-benzyl- 0.83 399 A 1001-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-30 (3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(4- 0.81 499 A  80((tert-butoxycarbonyl)amino)butyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-31(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-N- 0.85 424 A  22cyclohexylmethyl-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-32(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-  0.76, 426 A  93((tetrahydro-2H-pyran-2-yl)methyl)octahydro-6H-3,6- 0.75methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-33(3S*,3aS*,6S*,7R*,7aS*)-7-(4-aminobutyl)-N-benzyl- 0.62 399 A 1001-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-34 (3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(4- 0.82 499 A  78((tert-butoxycarbonyl)amino)butyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-353-((3S*,3aS*,6S*,7R*,7aS*)-3a-(benzylcarbamoyl)-1- 0.65 400 A 100isobutyloctahydro-1H-3,6-methanopyrrolo[3,2- c]pyridin-7-yl)propanoicacid IF-36 (3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3- 0.72 414 A— methoxy-3-oxopropyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-38(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-7- 0.86 424 A  83(cyclohexylmethyl)-1-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-39(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1- 0.86 458 A  62cyclohexylmethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-40(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(4- 0.75 468 A  63hydroxybenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-41(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(4-(tert- 0.90 524 A  52butoxy)benzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-42(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-(naphthalen- 0.88 502 A  651-ylmethyl)octahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-43 (3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-N,7-dibenzyl-1- 1.08 460 B  51isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-44 (3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-N,1,7- 1.04 392 B  82triisobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-45 (3S*,3aS*,6S*,7R*,7c]pyridine-6-carboxamideaS*)-4- 1.05 426 B  83acetyl-7-benzyl-N,1-diisobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-46(3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-1-benzyl-N,7- 1.05 426 B  79diisobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-47 (3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-N-benzyl-1,7- 1.06 426 B  88diisobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-49 (3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-N,1-dibenzyl-7- 1.08 460 B  84isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-50 (3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-N,1,7- 1.10 494 B  75tribenzyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-54 (3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-1-benzyl-7-isobutyl- 1.10 474 B 58 N-phenethyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-57(3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-7-benzyl-1-isobutyl- 1.12 474 B  40N-(3-methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-58(3S*,3aS*,6S*,7R*,7aS*)-4-acetyl-7-benzyl-1-isobutyl- 1.12 474 B  55N-(4-methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-68(3S*,3aS*,6S*,7R*,7aS*)-4-benzoyl-N,7-dibenzyl-1- 1.17 522 B  51isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-69 (3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-4-ethyl-1- 1.06 446 B  57isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-70 (3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isobutyl-4- 1.13 476 B  32(methoxycarbonyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-71(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-isobutyl-4- 1.02 432 B  38methyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-72 (3S*,3aS*,6S*,7R*,7aS*)-N,1-dibenzyl-4-ethyl-7- 1.06 446 B  45isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-73 tert-butyl (3S*,3aS*,6S*,7R*,7aS*)-6- 0.84 500 A  9(benzylcarbamoyl)-1-isobutyl-7-(2-carboxyethyl)octahydro-5H-3,6-methanopyrrolo[3,2-c]pyridine-5-carboxylate IF-74 tert-butyl (3S*,3aS*,6S*,7R*,7aS*)-3a-0.91 514 A  71 (benzylcarbamoyl)-1-isobutyl-7-(3-methoxy-3-oxopropyl)octahydro-4H-3,6-methanopyrrolo[3,2- b]pyridine-4-carboxylateIF-76 tert-butyl 3-((3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-6- 1.04 490 B  53(benzylcarbamoyl)octahydro-1H-3,6-methanopyrrolo[3,2-c]pyridin-1-yl)propanoate IF-77(3S*,3aS*,6S*,7R*,7aS*)-N,1-dibenzyl-7-(4- 0.93 468 B  60hydroxybenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-80(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-(naphthalen-1- 0.84 454 A  44ylmethyl)-7-propyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide

Compound Retention Mass Measurement number R₁ R₂ R₃ RT (min) (M + H)⁺condition IF-81  Cbm-M Np-M i-Bu 0.71 435 C IF-82  Cbm-M Np-M Bnzl 0.72469 C IF-83  Cbm-M Np-M 4-OH-Bnzl 0.67 485 C IF-84  Cbm-M Np-M i-Pnt0.73 449 C IF-85  Cbm-M Np-M Ph-Et 0.75 483 C IF-86  Cbm-M Ph-Et i-Bu0.66 399 C IF-87  Cbm-M Ph-Et Bnzl 0.68 433 C IF-88  Cbm-M Ph-Et4-OH-Bnzl 0.63 449 C IF-89  Cbm-M Ph-Et i-Pnt 0.70 413 C IF-90  Cbm-MPh-Et Np-M 0.74 483 C IF-91  Cbm-M Np-M Np-M 0.76 519 C IF-92  Cbm-M4-F-Bnzl i-Bu 0.65 403 C IF-93  Cbm-M 4-F-Bnzl Bnzl 0.67 437 C IF-94 Cbm-M 4-F-Bnzl 4-OH-Bnzl 0.62 453 C IF-95  Cbm-M 4-F-Bnzl i-Pnt 0.69 417C IF-96  Cbm-M 4-F-Bnzl Ph-Et 0.71 451 C IF-97  Cbm-M 4-F-Bnzl Np-M 0.73487 C IF-98  Cbm-M i-Pnt i-Bu 0.66 365 C IF-99  Cbm-M i-Pnt Bnzl 0.67399 C IF-100 Cbm-M i-Pnt 4-OH-Bnzl 0.62 415 C IF-101 Cbm-M i-Pnt Cbx-E0.58 381 C IF-102 Cbm-M i-Pnt Ph-Et 0.71 413 C IF-103 Cbm-M i-Pnt Np-M0.73 449 C IF-104 Cbm-M Hxy i-Bu 0.71 379 C IF-105 Cbm-M Hxy Bnzl 0.72413 C IF-106 Cbm-M Hxy 4-OH-Bnzl 0.67 429 C IF-107 Cbm-M Hxy Cbx-E 0.63395 C IF-108 Cbm-M Hxy i-Pnt 0.73 393 C IF-109 Cbm-M Hxy Ph-Et 0.75 427C IF-110 Cbm-M Hxy Np-M 0.77 463 C IF-111 Cbm-M i-Pr i-Bu 1.03 337 DIF-112 Cbm-M i-Pr Bnzl 0.58 371 C IF-113 Cbm-M i-Pr 4-OH-Bnzl 0.97 387 DIF-114 Cbm-M i-Pr Cbx-E 0.22 353 E IF-115 Cbm-M i-Pr i-Pnt 1.09 351 DIF-116 Cbm-M i-Pr Ph-Et 0.63 385 C IF-117 Cbm-M i-Pr Np-M 0.65 421 CIF-118 Cbm-M i-Bu i-Bu 0.62 351 C IF-119 Cbm-M i-Bu Bnzl 0.64 385 CIF-120 Cbm-M i-Bu 4-OH-Bnzl 0.59 401 C IF-121 Cbm-M i-Bu Cbx-E 0.93 367D IF-122 Cbm-M i-Bu i-Pnt 0.66 365 C IF-123 Cbm-M i-Bu Ph-Et 0.69 399 CIF-124 Cbm-M i-Bu Np-M 0.71 435 C IF-125 Cbm-M Bnzl i-Bu 0.65 385 CIF-126 Cbm-M Bnzl Bnzl 0.67 419 C IF-127 Cbm-M Bnzl 4-OH-Bnzl 0.62 435 CIF-128 Cbm-M Bnzl Cbx-E 0.99 401 D IF-129 Cbm-M Bnzl i-Pnt 0.69 399 CIF-130 Cbm-M Bnzl Ph-Et 0.71 433 C IF-131 Cbm-M Bnzl Np-M 0.73 469 CIF-132 Cbm-M 4-OH-Bnzl i-Bu 0.57 401 C IF-133 Cbm-M 4-OH-Bnzl Bnzl 0.59435 C IF-134 Cbm-M 4-OH-Bnzl Cbx-E 0.87 417 D IF-135 Cbm-M 4-OH-Bnzli-Pnt 0.60 415 C IF-136 Cbm-M 4-OH-Bnzl Ph-Et 0.63 449 C IF-137 Cbm-M4-OH-Bnzl Np-M 0.65 485 C IF-138 Cbm-M Cbx-E Bnzl 0.94 401 D IF-139Cbm-M Cbx-E 4-OH-Bnzl 0.47 417 D IF-140 Cbm-M Cbx-E Ph-Et 1.01 415 DIF-141 Cbm-M Cbx-E Np-M 0.60 451 C IF-142 Cbm-M Cbm-E i-Bu 0.23 366 EIF-143 Cbm-M Cbm-E Bnzl 0.88 400 D IF-144 Cbm-M Cbm-E 4-OH-Bnzl 0.23 416E IF-145 Cbm-M Cbm-E Cbx-E 0.20 382 E IF-146 Cbm-M Cbm-E i-Pnt 0.91 380D IF-147 Cbm-M Cbm-E Ph-Et 0.89 414 D IF-148 Cbm-M Cbm-E Np-M 0.57 450 CIF-149 Cbm-M Gun-Pr i-Bu 0.83 394 D IF-150 Cbm-M Gun-Pr Bnzl 0.92 428 DIF-151 Cbm-M Gun-Pr 4-OH-Bnzl 0.34  442¹ E IF-152 Cbm-M Gun-Pr i-Pnt0.93 408 D IF-153 Cbm-M Gun-Pr Ph-Et 0.96 442 D IF-154 Cbm-M Gun-Pr Np-M1.01 478 D IF-155 Cbm-M Hdr-E i-Bu 0.46 339 E IF-156 Cbm-M Hdr-E Bnzl0.49 373 C IF-157 Cbm-M Hdr-E 4-OH-Bnzl 0.35 389 E IF-158 Cbm-M Hdr-ECbx-E 0.20 355 E IF-159 Cbm-M Hdr-E i-Pnt 0.93 353 D IF-160 Cbm-M Hdr-EPh-Et 0.98 387 D IF-161 Cbm-M Hdr-E Np-M 0.58 423 C IF-162 Gun-Pr Np-Mi-Bu 1.25 477 D IF-163 Gun-Pr Np-M Bnzl 0.72 511 C IF-164 Gun-Pr Np-M4-OH-Bnzl 0.69 527 C IF-165 Gun-Pr Np-M i-Pnt 1.28 491 D IF-166 Gun-PrNp-M Ph-Et 0.75 525 C IF-167 Gun-Pr Np-M Np-M 1.31 561 D IF-168 Gun-PrHxy i-Pnt 0.74 435 C IF-169 Gun-Pr Hxy Ph-Et 1.30 469 D IF-170 Gun-PrHxy Np-M 1.33 505 D IF-171 Gun-Pr i-Pr i-Bu 1.08 379 D IF-172 Gun-Pri-Pr 4-OH-Bnzl 1.04 429 D IF-173 Gun-Pr i-Pr i-Pnt 1.12 393 D IF-174Gun-Pr i-Pr Ph-Et 1.15 427 D IF-175 Gun-Pr i-Pr Np-M 1.17 463 D IF-176Gun-Pr 4-F-Bnzl i-Bu 1.17 445 D IF-177 Gun-Pr 4-F-Bnzl Bnzl 0.68 479 CIF-178 Gun-Pr 4-F-Bnzl 4-OH-Bnzl 1.13 495 D IF-179 Gun-Pr 4-F-Bnzl i-Pnt1.21 459 D IF-180 Gun-Pr 4-F-Bnzl Ph-Et 0.71 493 C IF-181 Gun-Pr4-F-Bnzl Np-M 0.72 529 C IF-182 i-Bu Hdr-E Cbm-M 0.63 339 G IF-183 i-BuPh-Et Cbm-M 3.40 399 G IF-184 i-Bu Np-M Cbm-M 3.87 435 G IF-185 i-Bui-Bu Gun-Pr 3.15 393 G IF-186 i-Bu Bnzl Gun-Pr 3.42 427 G IF-187 i-Bu4-OH-Bnzl Gun-Pr 3.09 443 G IF-188 i-Bu Hdr-E Gun-Pr 1.17 381 G IF-189i-Bu Ph-Et Gun-Pr 3.57 441 G IF-190 i-Bu Np-M Gun-Pr 3.87 477 G IF-191i-Bu Hxy Gun-Pr 3.79 421 G IF-192 i-Bu 4-F-Bnzl Gun-Pr 3.49 445 G IF-193Bnzl Cbx-E Cbm-M 1.82 401 G IF-194 Bnzl Hdr-E Cbm-M 1.52 373 G IF-195Bnzl i-Pnt Cbm-M 3.59 399 G IF-196 Bnzl Ph-Et Cbm-M 3.62 433 G IF-197Bnzl i-Pr Cbm-M 3.02 371 G IF-198 Bnzl 4-OH-Bnzl Gun-Pr 3.54 477 GIF-199 Bnzl Hdr-E Gun-Pr 2.74 415 F IF-200 4-OH-Bnzl Ph-Et Gun-Pr 3.59491 G IF-201 4-OH-Bnzl Np-M Gun-Pr 3.90 527 G IF-202 Cbx-E i-Pr Cbm-M0.95 353 G IF-203 i-Pnt i-Bu Cbm-M 3.25 365 G IF-204 i-Pnt Bnzl Cbm-M3.47 399 F IF-205 i-Pnt 4-OH-Bnzl Cbm-M 3.13 415 G IF-206 i-Pnt Ph-EtCbm-M 2.43 413 F IF-207 i-Pnt Np-M Cbm-M 2.62 449 F IF-208 i-Pnt HxyCbm-M 3.97 393 G IF-209 i-Pnt i-Pr Cbm-M 2.97 351 G IF-210 i-Pnt4-F-Bnzl Cbm-M 3.60 417 G IF-211 i-Pnt Bnzl Gun-Pr 3.60 441 G IF-212i-Pnt Ph-Et Gun-Pr 3.79 455 G IF-213 i-Pnt Np-M Gun-Pr 2.63 491 G IF-214i-Pnt i-Pr Gun-Pr 3.25 393 G IF-215 i-Pnt 4-F-Bnzl Gun-Pr 3.72 459 GIF-216 Ph-Et Bnzl Cbm-M 2.45 433 F IF-217 Ph-Et 4-OH-Bnzl Cbm-M 3.40 449G IF-218 Ph-Et Cbx-E Cbm-M 2.85 415 G IF-219 Ph-Et Cbm-E Cbm-M 2.67 414G IF-220 Ph-Et Gun-Pr Cbm-M 2.94 442 G IF-221 Ph-Et Hdr-E Cbm-M 2.75 387G IF-222 Ph-Et i-Pnt Cbm-M 3.87 413 G IF-223 Ph-Et Np-M Cbm-M 2.75 483 FIF-224 Ph-Et 4-F-Bnzl Cbm-M 2.52 451 F IF-225 Ph-Et Hdr-E Gun-Pr 3.05429 G IF-226 Np-M i-Bu Cbm-M 2.49 435 F IF-227 Np-M Bnzl Cbm-M 2.62 469F IF-228 Np-M Cbm-E Cbm-M 3.27 450 G IF-229 Np-M Gun-Pr Cbm-M 3.32 478 GIF-230 Np-M Hdr-E Cbm-M 3.29 423 G IF-231 Np-M Ph-Et Cbm-M 2.65 483 FIF-232 Np-M Np-M Cbm-M 2.84 519 F IF-233 Np-M i-Pr Cbm-M 3.62 421 GIF-234 Np-M 4-F-Bnzl Cbm-M 2.65 487 F IF-235 Np-M i-Bu Gun-Pr 3.70 477 GIF-236 Np-M Bnzl Gun-Pr 3.88 511 G IF-237 Np-M 4-OH-Bnzl Gun-Pr 3.62 527G IF-238 Np-M Cbm-E Gun-Pr 3.22 492 G IF-239 Np-M Hdr-E Gun-Pr 3.20 465G IF-240 Np-M i-Pnt Gun-Pr 3.95 491 G IF-241 Np-M Ph-Et Gun-Pr 4.07 525G IF-242 Np-M Np-M Gun-Pr 4.27 561 G IF-243 Np-M Hxy Gun-Pr 4.25 505 GIF-244 Np-M i-Pr Gun-Pr 2.38 463 F IF-245 Np-M 4-F-Bnzl Gun-Pr 3.95 529G IF-246 Chm Bnzl Cbm-M 3.75 425 G IF-247 Chm 4-OH-Bnzl Cbm-M 3.40 441 GIF-248 Chm Cbx-E Cbm-M 2.90 407 G IF-249 Chm Cbm-E Cbm-M 2.74 406 GIF-250 Chm i-Pnt Cbm-M 2.50 405 F IF-251 Chm Ph-Et Cbm-M 2.52 439 FIF-252 Chm Np-M Cbm-M 2.69 475 F IF-253 Chm Hxy Cbm-M 4.17 419 G IF-254Chm i-Pr Cbm-M 3.29 377 F IF-255 Chm 4-F-Bnzl Cbm-M 2.54 443 F IF-256Chm Bnzl Gun-Pr 3.79 467 G IF-257 Chm i-Pnt Gun-Pr 3.90 447 G IF-258 ChmPh-Et Gun-Pr 3.95 481 G IF-259 Chm Np-M Gun-Pr 4.27 517 G IF-260 Chm HxyGun-Pr 4.12 461 G IF-261 Chm 4-F-Bnzl Gun-Pr 3.95 485 G IF-262 4-F-Bnzli-Bu Cbm-M 3.34 403 G IF-263 4-F-Bnzl Bnzl Cbm-M 3.57 437 G IF-2644-F-Bnzl 4-OH-Bnzl Cbm-M 3.22 453 G IF-265 4-F-Bnzl Cbx-E Cbm-M 2.34 419G IF-266 4-F-Bnzl Cbm-E Cbm-M 1.63 418 G IF-267 4-F-Bnzl Hdr-E Cbm-M1.79 391 G IF-268 4-F-Bnzl i-Pnt Cbm-M 3.70 417 G IF-269 4-F-Bnzl Ph-EtCbm-M 2.43 451 F IF-270 4-F-Bnzl Np-M Cbm-M 2.62 487 F IF-271 4-F-BnzlHxy Cbm-M 2.60 431 F IF-272 4-F-Bnzl i-Pr Cbm-M 3.10 389 G IF-2734-F-Bnzl Hdr-E Gun-Pr 2.70 433 G IF-274 4-F-Bnzl i-Pr Gun-Pr 3.37 431 GIF-275 Cbx-E i-Bu Cbm-M 3.20 367 G IF-276 Cbx-E i-Pnt Cbm-M 3.54 381 GIF-277 Bnzl Bnzl Cbm-M 2.38 419 F IF-278 Bnzl Np-M Cbm-M 4.09 469 GIF-279 Bnzl Hxy Cbm-M 4.02 413 G IF-280 Bnzl 4-F-Bnzl Cbm-M 2.43 437 FIF-281 Bnzl Bnzl Gun-Pr 2.40 461 F IF-282 Bnzl i-Pnt Gun-Pr 2.47 441 FIF-283 Bnzl Ph-Et Gun-Pr 2.50 475 F IF-284 Bnzl Np-M Gun-Pr 2.62 511 FIF-285 Bnzl Hxy Gun-Pr 2.62 455 F IF-286 Bnzl 4-F-Bnzl Gun-Pr 2.47 479 FIF-287 Ph-Et Bnzl Gun-Pr 2.52 475 F IF-288 Ph-Et 4-OH-Bnzl Gun-Pr 2.38491 F IF-289 Ph-Et i-Pnt Gun-Pr 2.57 455 F IF-290 Ph-Et Np-M Gun-Pr 2.72525 F IF-291 Ph-Et Hxy Gun-Pr 2.70 469 F IF-292 Ph-Et 4-F-Bnzl Gun-Pr2.59 493 F IF-293 4-F-Bnzl i-Bu Gun-Pr 2.34 445 F IF-294 4-F-Bnzl BnzlGun-Pr 2.43 479 F IF-295 4-F-Bnzl i-Pnt Gun-Pr 2.50 459 F IF-2964-F-Bnzl Ph-Et Gun-Pr 2.50 493 F IF-297 4-F-Bnzl Np-M Gun-Pr 2.63 529 FIF-298 4-F-Bnzl Hxy Gun-Pr 2.63 473 F IF-299 i-Bu Cbm-E Cbx-E 1.03 381 HIF-300 i-Bu Cbm-E i-Pnt 2.15 379 H IF-301 i-Bu Gun-Pr i-Bu 2.13 393 HIF-302 i-Bu Gun-Pr Bnzl 2.19 427 H IF-303 i-Bu Gun-Pr 4-OH-Bnzl 1.79 443H IF-304 i-Bu Gun-Pr i-Pnt 1.95 407 H IF-305 i-Bu Gun-Pr Ph-Et 1.98 441H IF-306 i-Bu Gun-Pr Np-M 2.08 477 H IF-307 Bnzl Cbm-E Cbx-E 1.76 415 HIF-308 Bnzl Cbm-E i-Pnt 2.02 413 H IF-309 Bnzl Gun-Pr i-Bu 1.82 427 HIF-310 Bnzl Gun-Pr Bnzl 2.02 461 H IF-311 Bnzl Gun-Pr 4-OH-Bnzl 1.87 477H IF-312 Bnzl Gun-Pr i-Pnt 2.05 441 H IF-313 Bnzl Gun-Pr Ph-Et 2.08 475H IF-314 Bnzl Gun-Pr Np-M 2.14 511 H IF-315 4-OH-Bnzl Cbm-E Cbx-E 1.28431 H IF-316 4-OH-Bnzl Cbm-E i-Pnt 1.85 429 H IF-317 4-OH-Bnzl Gun-Pri-Bu 1.85 443 H IF-318 4-OH-Bnzl Gun-Pr Bnzl 1.91 477 H IF-319 4-OH-BnzlGun-Pr i-Pnt 1.89 457 H IF-320 4-OH-Bnzl Gun-Pr Ph-Et 1.96 491 H IF-3214-OH-Bnzl Gun-Pr Np-M 2.00 527 H IF-322 Cbx-E Cbm-E i-Pnt 1.73 395 HIF-323 Gun-Pr i-Bu i-Bu 1.98 393 H IF-324 Gun-Pr i-Bu Bnzl 1.99 427 HIF-325 Gun-Pr i-Bu 4-OH-Bnzl 1.92 443 H IF-326 Gun-Pr i-Bu i-Pnt 2.10407 H IF-327 Gun-Pr i-Bu Ph-Et 2.15 441 H IF-328 Gun-Pr i-Bu Np-M 2.14477 H IF-329 Gun-Pr Bnzl i-Bu 2.06 427 H IF-330 Gun-Pr Bnzl Bnzl 2.08461 H IF-331 Gun-Pr Bnzl 4-OH-Bnzl 1.98  47 H IF-332 Gun-Pr Bnzl i-Pnt2.16 441 H IF-333 Gun-Pr Bnzl Ph-Et 2.19 475 H IF-334 Gun-Pr Bnzl Np-M2.21 511 H IF-335 Gun-Pr 4-OH-Bnzl i-Bu 1.89 443 H IF-336 Gun-Pr4-OH-Bnzl Bnzl 1.95 477 H IF-337 Gun-Pr 4-OH-Bnzl i-Pnt 1.92 457 HIF-338 Gun-Pr 4-OH-Bnzl Ph-Et 1.97 491 H IF-339 Gun-Pr 4-OH-Bnzl Np-M2.01 527 H IF-340 Gun-Pr Cbm-E i-Bu 1.64 408 H IF-341 Gun-Pr Cbm-E Bnzl1.72 442 H IF-342 Gun-Pr Cbm-E 4-OH-Bnzl 1.15 458 H IF-343 Gun-Pr Cbm-Ei-Pnt 1.73 422 H IF-344 Gun-Pr Cbm-E Ph-Et 1.79 456 H IF-345 Gun-PrCbm-E Np-M 1.84 492 H IF-346 Gun-Pr Hdr-E i-Bu 1.70 381 H IF-347 Gun-PrHdr-E Bnzl 1.73 415 H IF-348 Gun-Pr Hdr-E 4-OH-Bnzl 1.59 431 H IF-349Gun-Pr Hdr-E i-Pnt 1.78 395 H IF-350 Gun-Pr Hdr-E Ph-Et 1.82 429 HIF-351 Gun-Pr Hdr-E Np-M 1.84 465 H IF-352 Gun-Pr i-Pnt i-Bu 2.07 407 HIF-353 Gun-Pr i-Pnt Bnzl 2.10 441 H IF-354 Gun-Pr i-Pnt 4-OH-Bnzl 2.02457 H IF-355 Gun-Pr i-Pnt Ph-Et 2.12 455 H IF-356 Gun-Pr i-Pnt Np-M 2.22491 H IF-357 Gun-Pr Ph-Et i-Bu 2.09 441 H IF-358 Gun-Pr Ph-Et Bnzl 2.10475 H IF-359 Gun-Pr Ph-Et 4-OH-Bnzl 2.02 491 H IF-360 Gun-Pr Ph-Et i-Pnt2.18 455 H IF-361 Gun-Pr Ph-Et Np-M 2.19 525 H IF-362 Hdr-E Cbm-E Cbx-E0.41 369 H IF-363 Hdr-E Cbm-E i-Pnt 1.71 367 H IF-364 Hdr-E Gun-Pr i-Bu1.64 381 H IF-365 Hdr-E Gun-Pr Bnzl 1.76 415 H IF-366 Hdr-E Gun-Pr4-OH-Bnzl 1.84 431 H IF-367 Hdr-E Gun-Pr i-Pnt 1.75 395 H IF-368 Hdr-EGun-Pr Ph-Et 1.81 429 H IF-369 Hdr-E Gun-Pr Np-M 1.83 465 H IF-370 i-PntCbm-E Cbx-E 1.75 395 H IF-371 i-Pnt Gun-Pr i-Bu 2.01 407 H IF-372 i-PntGun-Pr Bnzl 2.05 441 H IF-373 i-Pnt Gun-Pr 4-OH-Bnzl 1.91 H IF-374 i-PntGun-Pr Ph-Et 2.09 455 H IF-375 i-Pnt Gun-Pr Np-M 2.15 491 H IF-376 Ph-EtCbm-E Cbx-E 1.85 429 H IF-377 Ph-Et Cbm-E i-Pnt 2.09 427 H IF-378 Ph-EtGun-Pr i-Bu 2.05 441 H IF-379 Ph-Et Gun-Pr Bnzl 2.18 H IF-380 Ph-EtGun-Pr 4-OH-Bnzl 1.94 491 H IF-381 Ph-Et Gun-Pr i-Pnt 2.11 455 H IF-382Ph-Et Gun-Pr Np-M 2.20 525 H IF-383 Np-M Cbm-E Cbx-E 1.91 465 H IF-384Np-M Cbm-E i-Pnt 2.17 463 H IF-385 Np-M Gun-Pr i-Bu 1.82 477 H IF-386Np-M Gun-Pr Bnzl 2.15 511 H IF-387 Np-M Gun-Pr 4-OH-Bnzl 1.97 527 HIF-388 Np-M Gun-Pr i-Pnt 2.17 491 H IF-389 Np-M Gun-Pr Ph-Et 2.20 525 HIF-390 Np-M Gun-Pr Np-M 2.22 561 H IF-391 Chm Cbm-E Cbx-E 1.83 421 HIF-392 Chm Cbm-E i-Pnt 2.10 419 H IF-393 Chm Gun-Pr i-Bu 2.06 433 HIF-394 Chm Gun-Pr Bnzl 2.13 467 H IF-395 Chm Gun-Pr 4-OH-Bnzl 1.91 483 HIF-396 Chm Gun-Pr i-Pnt 2.13 447 H IF-397 Chm Gun-Pr Ph-Et 2.15 481 HIF-398 Chm Gun-Pr Np-M 2.22 517 H IF-399 4-F-Bnzl Cbm-E Cbx-E 1.78 433 HIF-400 4-F-Bnzl Cbm-E i-Pnt 2.06 431 H IF-401 4-F-Bnzl Gun-Pr i-Bu 2.03445 H IF-402 4-F-Bnzl Gun-Pr Bnzl 2.10 479 H IF-403 4-F-Bnzl Gun-Pr4-OH-Bnzl 1.90 495 H IF-404 4-F-Bnzl Gun-Pr i-Pnt 2.10 459 H IF-4054-F-Bnzl Gun-Pr Ph-Et 2.13 493 H IF-406 4-F-Bnzl Gun-Pr Np-M 2.19 529 HIF-407 Ph-Et i-Bu i-Pnt 1.54 412 I IF-408 Np-M i-Bu i-Pnt 1.68 448 IIF-409 Chm i-Bu i-Pnt 1.55 404 I IF-410 4-F-Bnzl i-Bu i-Pnt 1.51 416 IIF-411 Bnzl i-Bu i-Pnt 1.46 398 I IF-412 i-Bu i-Bu i-Pnt 1.40 364 IIF-413 i-Pnt Cbx-E Np-M 1.41 464 I IF-414 i-Pnt Cbx-E i-Bu 1.15 380 IIF-415 Chm Cbx-E i-Pnt 1.15 420 I IF-416 Chm Cbx-E Np-M 1.51 490 IIF-417 4-F-Bnzl Cbx-E Np-M 1.46 502 I IF-418 i-Pnt 4-F-Bnzl Cbx-E 1.18432 I IF-419 Chm Np-M Cbx-E 1.40 490 I IF-420 4-F-Bnzl Np-M Cbx-E 1.42502 I IF-421 Cbx-E 4-F-Bnzl i-Bu 1.27 418 I IF-422 Cbx-E Np-M i-Pnt 1.48464 I IF-423 Cbx-E 4-F-Bnzl Np-M 1.47 502 I IF-424 Cbx-E i-Bu Bnzl 1.20400 I IF-425 Cbx-E 4-OH-Bnzl Np-M 1.28 500 I IF-426 Bnzl Hxy Cbx-E 1.31428 I IF-427 i-Bu Hxy Cbx-E 1.24 394 I IF-428 i-Bu Cbx-E Np-M 1.35 450 IIF-429 i-Bu Cbx-E i-Bu 1.02 366 I IF-430 Hdr-E i-Bu i-Pnt 1.23 352 IIF-431 Ph-Et i-Bu Np-M 1.75 482 I IF-432 Np-M i-Bu Ph-Et 1.75 482 IIF-433 Np-M i-Bu Np-M 1.96 518 I IF-434 Np-M i-Bu Bnzl 1.73 468 I IF-435Np-M Cbm-E 4-OH-Bnzl 1.17 499 I IF-436 4-F-Bnzl i-Bu Np-M 1.73 486 IIF-437 i-Pnt Ph-Et i-Bu 1.55 412 I IF-438 Ph-Et Hxy i-Bu 1.67 426 IIF-439 Chm Ph-Et 4-OH-Bnzl 1.43 488 I IF-440 4-F-Bnzl Ph-Et Np-M 1.77534 I IF-441 Bnzl i-Bu Np-M 1.65 468 I IF-442 4-OH-Bnzl Hdr-E Np-M 1.26472 I IF-443 4-OH-Bnzl i-Bu i-Pnt 1.25 414 I IF-444 Hdr-E Cbx-E Np-M1.15 438 I IF-445 i-Pnt 4-OH-Bnzl Cbx-E 0.97 430 I IF-446 Chm Cbx-E i-Bu1.25 406 I IF-447 Chm 4-OH-Bnzl Cbx-E 1.12 456 I IF-448 Np-M Hdr-E Cbx-E1.13 438 I IF-449 Cbx-E Np-M i-Bu 1.43 450 I IF-450 Cbx-E Hxy i-Bu 1.43394 I IF-451 Cbx-E Hdr-E Ph-Et 0.91 402 I IF-452 Cbx-E Hdr-E Np-M 1.13438 I IF-453 Cbx-E 4-F-Bnzl Ph-Et 1.41 466 I IF-454 Cbx-E i-Bu Ph-Et1.30 414 I IF-455 Cbx-E i-Bu 4-OH-Bnzl 1.11 416 I IF-456 Cbx-E Cbm-EPh-Et 0.95 429 I IF-457 Cbx-E Cbm-E Np-M 1.16 465 I IF-458 Cbx-E4-OH-Bnzl i-Pnt 1.13 430 I IF-459 Bnzl Cbx-E Np-M 1.42 484 I IF-460 i-BuNp-M Cbx-E 1.32 450 I IF-461 4-OH-Bnzl Np-M Cbx-E 1.26 I IF-462 Hdr-E4-OH-Bnzl Ph-Et 1.20 I IF-463 Hdr-E 4-OH-Bnzl Np-M 1.27 472 I IF-464i-Pnt 4-OH-Bnzl Ph-Et 1.40 462 I IF-465 i-Pnt 4-OH-Bnzl Np-M 1.53 498 IIF-466 i-Pnt 4-OH-Bnzl Bnzl 1.37 448 I IF-467 i-Pnt 4-OH-Bnzl i-Bu 1.32414 I IF-468 Ph-Et 4-OH-Bnzl i-Pnt 1.48 462 I IF-469 Ph-Et 4-OH-BnzlBnzl 1.46 482 I IF-470 Ph-Et 4-OH-Bnzl i-Bu 1.38 448 I IF-471 Np-M4-OH-Bnzl i-Pnt 1.63 498 I IF-472 Np-M 4-OH-Bnzl Bnzl 1.58 518 I IF-473Np-M 4-OH-Bnzl i-Bu 1.51 484 I IF-474 Chm 4-OH-Bnzl i-Pnt 1.46 454 IIF-475 Chm 4-OH-Bnzl Ph-Et 1.49 488 I IF-476 Chm 4-OH-Bnzl Np-M 1.62 524I IF-477 Chm 4-OH-Bnzl Bnzl 1.43 474 I IF-478 Chm 4-OH-Bnzl i-Bu 1.41440 I IF-479 4-F-Bnzl 4-OH-Bnzl i-Pnt 1.41 466 I IF-480 4-F-Bnzl4-OH-Bnzl Np-M 1.58 536 I IF-481 4-F-Bnzl 4-OH-Bnzl Bnzl 1.38 486 IIF-482 4-F-Bnzl 4-OH-Bnzl i-Bu 1.32 452 I IF-483 i-Pnt Hdr-E Bnzl 1.23386 I IF-484 Ph-Et Hdr-E Bnzl 1.30 420 I IF-485 Np-M Hdr-E 4-OH-Bnzl1.17 472 I IF-486 Chm Hdr-E Bnzl 1.33 412 I IF-487 4-F-Bnzl Hdr-E Bnzl1.24 424 I IF-488 4-F-Bnzl Hdr-E 4-OH-Bnzl 0.75 440 I IF-489 i-Pnt Hdr-EPh-Et 1.29 400 I IF-490 4-F-Bnzl Hdr-E i-Pnt 1.30 404 I IF-491 4-F-BnzlHdr-E Ph-Et 1.34 438 I IF-492 Bnzl Hdr-E i-Bu 1.17 372 I IF-493 Bnzl4-OH-Bnzl i-Pnt 1.40 448 I IF-494 Bnzl 4-OH-Bnzl Bnzl 1.37 468 I IF-495Bnzl 4-OH-Bnzl i-Bu 1.29 434 I IF-497 i-Bu Hdr-E i-Pnt 1.12 352 I IF-498i-Bu Hdr-E Ph-Et 1.18 386 I IF-499 i-Bu 4-OH-Bnzl i-Pnt 1.29 414 IIF-500 i-Bu 4-OH-Bnzl Np-M 1.46 484 I IF-501 i-Bu 4-OH-Bnzl i-Bu 1.22400 I IF-502 4-OH-Bnzl Hdr-E i-Pnt 0.99 402 I IF-503 4-OH-Bnzl i-Pri-Pnt 1.20 400 I IF-504 4-OH-Bnzl i-Pr Np-M 1.39 470 I IF-505 Np-M Bnzl4-OH-Bnzl 1.46 518 I IF-506 4-F--Bnzl Bnzl Np-M 1.73 520 I IF-507 Hdr-EHxy i-Bu 1.43 366 I IF-508 Hdr-E 4-F-Bnzl Bnzl 1.31 424 I IF-509 i-Pnt4-F-Bnzl 4-OH-Bnzl 1.40 466 I IF-510 Ph-Et Hxy 4-OH-Bnzl 1.59 476 IIF-511 Np-M Hxy i-Bu 1.89 462 I IF-512 Np-M Hxy 4-OH-Bnzl 1.69 512 IIF-513 Chm Hxy i-Bu 1.75 418 I IF-514 Chm Hxy 4-OH-Bnzl 1.49 468 IIF-515 Hdr-E 4-F-Bnzl i-Pnt 1.42 404 I IF-516 Hdr-E 4-F-Bnzl Ph-Et 1.41438 I IF-517 Ph-Et Hxy i-Pnt 1.83 440 I IF-518 Np-M Hdr-E Ph-Et 1.46 470I IF-519 Np-M Hxy i-Pnt 1.98 476 I IF-520 Chm Hxy i-Pnt 1.81 432 IIF-521 Chm 4-F-Bnzl Ph-Et 1.67 490 I IF-522 4-F--Bnzl Hxy Ph-Et 1.85 478I IF-523 i-Bu Hxy 4-OH-Bnzl 1.46 428 I IF-524 i-Bu 4-F-Bnzl 4-OH-Bnzl1.37 452 I IF-525 i-Bu 4-F-Bnzl Ph-Et 1.63 450 I IF-526 Np-M i-Bu Cbx-E1.39 450 I IF-527 Ph-Et i-Pnt Cbx-E 1.35 428 I IF-528 Cbx-E i-Pnt Bnzl1.41 414 I IF-529 Cbx-E i-Pnt Ph-Et 1.46 428 I IF-530 Cbx-E i-Bu i-Pnt1.30 380 I IF-531 Hdr-E Cbm-E Np-M 1.10 437 I IF-532 Hdr-E Cbm-E i-Bu1.26 353 I IF-533 Hdr-E 4-OH-Bnzl i-Bu 1.47 388 I IF-534 Ph-Et 4-OH-BnzlNp-M 1.55 532 I IF-535 Np-M Cbm-E i-Bu 1.36 449 I IF-536 Chm Cbm-E Np-M1.51 489 I IF-537 Chm Cbm-E 4-OH-Bnzl 1.01 455 I IF-538 4-F-Bnzl Cbm-EPh-Et 1.31 465 I IF-539 4-F-Bnzl Cbm-E Np-M 1.41 501 I IF-540 Hdr-EPh-Et Bnzl 1.32 420 I IF-541 Hdr-E Ph-Et 4-OH-Bnzl 1.25 436 I IF-542Hdr-E Np-M i-Bu 1.42 422 I IF-543 Hdr-E Np-M 4-OH-Bnzl 1.34 I IF-544Hdr-E 4-F-Bnzl i-Bu 1.21 390 I IF-545 i-Pnt Ph-Et 4-OH-Bnzl 1.36 462 IIF-546 i-Pnt Hxy i-Bu 1.61 392 I IF-547 i-Pnt 4-F-Bnzl Bnzl 1.58 450 IIF-548 i-Pnt 4-F-Bnzl i-Bu 1.48 416 I IF-549 Ph-Et 4-F-Bnzl Bnzl 1.62484 I IF-550 Ph-Et 4-F-Bnzl i-Bu 1.56 450 I IF-551 Chm Np-M i-Bu 1.75474 I IF-552 4-F-Bnzl Np-M 4-OH-Bnzl 1.48 536 I IF-553 Hdr-E Ph-Et i-Pnt1.37 400 I IF-554 i-Pnt Hxy Ph-Et 1.77 440 I IF-555 i-Pnt Hxy Np-M 1.84476 I IF-556 Ph-Et 4-F-Bnzl i-Pnt 1.66 464 I IF-557 Chm 4-F-Bnzl i-Pnt1.66 456 I IF-558 4-F-Bnzl Np-M i-Pnt 1.73 500 I IF-559 Bnzl Hxy Bnzl1.70 446 I IF-560 Bnzl Hxy i-Bu 1.63 412 I IF-561 Bnzl 4-F-Bnzl Bnzl1.55 470 I IF-562 Bnzl Hxy i-Pnt 1.67 426 I IF-563 Bnzl Hxy Ph-Et 1.74460 I IF-564 Bnzl Cbm-E Ph-Et 1.31 447 I IF-565 Bnzl 4-OH-Bnzl Ph-Et1.45 482 I IF-566 Bnzl 4-OH-Bnzl Np-M 1.53 518 I IF-567 i-Bu Ph-Et4-OH-Bnzl 1.33 448 I IF-568 i-Bu Np-M 4-OH-Bnzl 1.42 484 I IF-569 i-BuHxy i-Bu 1.53 378 I IF-570 i-Bu Np-M i-Pnt 1.61 448 I IF-571 i-Bu Hxyi-Pnt 1.61 392 I IF-572 i-Bu Hxy Ph-Et 1.66 426 I IF-573 i-Bu Hxy Np-M1.83 462 I IF-574 i-Bu 4-F-Bnzl Np-M 1.67 486 I IF-575 i-Bu Cbm-E Ph-Et1.19 413 I IF-576 i-Bu 4-OH-Bnzl Ph-Et 1.31 448 I IF-577 4-OH-Bnzl Ph-EtBnzl 1.44 482 I IF-578 4-OH-Bnzl Np-M i-Bu 1.47 484 I IF-579 4-OH-BnzlHdr-E Ph-Et 1.59 436 I IF-580 4-OH-Bnzl Ph-Et Np-M 1.61 532 I IF-581Np-M 4-OH-Bnzl Ph-Et 1.64 532 I IF-582 Np-M 4-OH-Bnzl Np-M 1.80 568 IIF-583 i-Pnt Hxy 4-OH-Bnzl 1.50 442 I IF-584 4-F-Bnzl i-Pnt Bnzl 1.65450 I IF-585 4-F-Bnzl i-Pnt i-Bu 1.57 416 I IF-586 4-F-Bnzl Ph-Et Bnzl1.69 484 I IF-587 4-F-Bnzl Hxy Bnzl 1.79 464 I IF-588 Chm 4-F-Bnzl Np-M1.79 526 I IF-589 4-F-Bnzl i-Pnt Np-M 1.82 500 I IF-590 4-OH-Bnzl Ph-Eti-Bu 1.40 448 I IF-591 i-Pnt Bnzl Cbx-E 1.23 414 I IF-592 Ph-Et BnzlCbx-E 1.31 448 I IF-593 Np-M i-Pnt Cbx-E 1.51 464 I IF-594 Cbx-E i-BuNp-M 1.43 450 I IF-595 Bnzl Bnzl Cbx-E 1.19 434 I IF-596 Np-M i-Pr Np-M1.81 504 I IF-597 i-Pnt Hdr-E i-Bu 1.13 352 I IF-598 i-Pnt Hdr-E4-OH-Bnzl 0.61 402 I IF-599 i-Pnt Hxy Bnzl 1.67 426 I IF-600 Ph-Et Hdr-Ei-Bu 1.23 386 I IF-601 Ph-Et Hdr-E 4-OH-Bnzl 1.01 436 I IF-602 Ph-Et HxyBnzl 1.75 460 I IF-603 Np-M Hdr-E Bnzl 1.49 456 I IF-604 Np-M Hdr-E i-Bu1.35 422 I IF-605 Np-M Hxy Bnzl 1.92 496 I IF-606 Chm Hdr-E i-Bu 1.23378 I IF-607 Chm Hdr-E 4-OH-Bnzl 0.99 428 I IF-608 Chm 4-F-Bnzl Bnzl1.61 476 I IF-609 4-F-Bnzl Hdr-E i-Bu 1.17 390 I IF-610 Hdr-E Ph-Et Np-M1.48 470 I IF-611 i-Pnt Hdr-E Np-M 1.45 436 I IF-612 Ph-Et Hdr-E Np-M1.44 470 I IF-613 Np-M Hdr-E i-Pnt 1.43 436 I IF-614 Np-M Hdr-E Np-M1.59 506 I IF-615 Np-M Hxy Ph-Et 1.96 510 I IF-616 Np-M Hxy Np-M 2.10546 I IF-617 Chm Hdr-E i-Pnt 1.35 392 I IF-618 Chm Hdr-E Ph-Et 1.39 426I IF-619 Chm Hdr-E Np-M 1.46 462 I IF-620 4-F--Bnzl Hdr-E Np-M 1.43 474I IF-621 Bnzl Hdr-E Bnzl 1.22 406 I IF-622 Bnzl Hdr-E 4-OH-Bnzl 0.75 422I IF-623 Bnzl Hdr-E Ph-Et 1.31 420 I IF-624 Bnzl Hdr-E Np-M 1.42 456 IIF-625 i-Bu Hdr-E Np-M 1.33 422 I IF-627 Hdr-E Bnzl i-Pnt 1.34 386 IIF-628 Hdr-E Bnzl Bnzl 1.30 406 I IF-629 Hdr-E Bnzl i-Bu 1.25 372 IIF-630 Hdr-E Bnzl 4-OH-Bnzl 1.22 422 I IF-631 Hdr-E i-Bu i-Bu 1.15 338 IIF-632 i-Pnt Bnzl Ph-Et 1.62 446 I IF-634 i-Pnt Bnzl 4-OH-Bnzl 1.31 448I IF-635 i-Pnt i-Bu Ph-Et 1.54 412 I IF-636 i-Pnt i-Bu i-Bu 1.42 364 IIF-637 i-Pnt i-Bu 4-OH-Bnzl 1.30 414 I IF-638 Ph-Et Bnzl i-Pnt 1.66 446I IF-639 Ph-Et Bnzl i-Bu 1.56 432 I IF-640 Ph-Et Bnzl 4-OH-Bnzl 1.40 482I IF-641 Ph-Et i-Bu Bnzl 1.58 432 I IF-642 Np-M Bnzl i-Bu 1.73 468 IIF-643 Chm Bnzl Ph-Et 1.66 472 I IF-644 Chm Bnzl i-Bu 1.59 424 I IF-645Chm Bnzl 4-OH-Bnzl 1.34 474 I IF-646 Chm i-Bu Np-M 1.76 474 I IF-647 Chmi-Bu 4-OH-Bnzl 1.35 440 I IF-648 4-F-Bnzl Bnzl Ph-Et 1.68 484 I IF-6494-F-Bnzl Bnzl Bnzl 1.60 470 I IF-650 4-F-Bnzl Bnzl i-Bu 1.57 436 IIF-651 4-F-Bnzl Bnzl 4-OH-Bnzl 1.32 486 I IF-652 4-F-Bnzl i-Bu Ph-Et1.59 450 I IF-653 4-F-Bnzl i-Bu Bnzl 1.52 436 I IF-654 4-F-Bnzl i-Bui-Bu 1.48 402 I IF-655 4-F-Bnzl i-Bu 4-OH-Bnzl 1.29 452 I IF-656 Hdr-Ei-Pnt Bnzl 1.36 386 I IF-657 Ph-Et i-Pnt i-Bu 1.62 412 I IF-658 Chmi-Pnt Bnzl 1.65 438 I IF-659 Chm i-Pnt i-Bu 2.29 404 I IF-660 Hdr-Ei-Pnt Np-M 1.53 436 I IF-661 Np-M i-Pnt Ph-Et 1.91 496 I IF-662 Chmi-Pnt Ph-Et 1.72 452 I IF-663 Chm i-Pnt Np-M 1.83 488 I IF-664 4-F-Bnzli-Pnt Ph-Et 1.68 464 I IF-665 Bnzl i-Pnt Bnzl 1.61 432 I IF-666 Bnzli-Pnt 4-OH-Bnzl 1.36 448 I IF-667 Bnzl i-Pnt Ph-Et 1.65 446 I IF-670Bnzl i-Bu Ph-Et 1.54 432 I IF-671 i-Bu i-Pnt i-Bu 1.44 364 I IF-672 i-Bui-Pnt 4-OH-Bnzl 1.30 414 I IF-673 i-Bu i-Pnt Ph-Et 1.56 412 I IF-674i-Bu i-Pnt Np-M 1.71 448 I IF-675 i-Bu Bnzl i-Pnt 1.53 398 I IF-678 i-BuBnzl 4-OH-Bnzl 1.23 434 I IF-679 i-Bu i-Bu Ph-Et 1.48 398 I IF-680 i-Bui-Bu Np-M 1.59 434 I IF-683 i-Bu i-Bu 4-OH-Bnzl 1.23 400 I IF-6844-OH-Bnzl i-Pnt Np-M 1.62 498 I IF-686 i-Pnt Cbm-E Ph-Et 1.28 427 IIF-687 Np-M i-Pnt 4-OH-Bnzl 1.56 498 I IF-688 Chm 4-F-Bnzl i-Bu 1.56 442I IF-689 4-F-Bnzl Hxy 4-OH-Bnzl 1.47 480 I IF-690 Ph-Et Hdr-E i-Pnt 1.30400 I IF-691 Bnzl i-Pnt i-Bu 1.54 398 I IF-692 Bnzl Hxy 4-OH-Bnzl 1.45462 I IF-693 Cbx-E Bnzl Bnzl 1.30 434 I IF-694 Cbx-E Bnzl i-Bu 1.24 400I IF-695 Bnzl i-Pnt Cbx-E 1.26 414 I IF-696 i-Pnt Cbm-E Np-M 1.46 463 IIF-697 i-Pnt Cbm-E Bnzl 1.28 413 I IF-698 Ph-Et Cbm-E Bnzl 1.36 447 IIF-699 Ph-Et Cbm-E i-Bu 1.24 413 I IF-700 Chm Cbm-E Ph-Et 1.43 453 IIF-701 Chm Cbm-E Bnzl 1.36 439 I IF-702 4-F-Bnzl Cbm-E Bnzl 1.27 451 IIF-703 4-F-Bnzl Cbm-E i-Bu 1.23 417 I IF-704 Hdr-E Ph-Et i-Bu 1.31 386 IIF-705 i-Pnt Np-M i-Bu 1.69 448 I IF-706 i-Pnt Np-M 4-OH-Bnzl 1.50 498 IIF-707 Ph-Et i-Pnt 4-OH-Bnzl 1.47 462 I IF-708 Np-M Ph-Et 4-OH-Bnzl 1.57532 I IF-709 Chm i-Pnt 4-OH-Bnzl 1.40 454 I IF-710 Chm Ph-Et Bnzl 1.72472 I IF-711 Chm Ph-Et i-Bu 1.69 438 I IF-712 Chm Np-M 4-OH-Bnzl 1.58524 I IF-713 4-F-Bnzl i-Pnt 4-OH-Bnzl 1.38 466 I IF-714 4-F-Bnzl Ph-Eti-Bu 1.62 450 I IF-715 4-F-Bnzl Ph-Et 4-OH-Bnzl 1.42 500 I IF-7164-F-Bnzl Np-M i-Bu 1.71 486 I IF-717 Chm Ph-Et i-Pnt 1.76 452 I IF-718Chm Ph-Et Np-M 1.94 522 I IF-719 Chm Np-M i-Pnt 1.81 488 I IF-7204-F-Bnzl Ph-Et i-Pnt 1.68 464 I IF-721 Bnzl Ph-Et i-Bu 1.58 432 I IF-722Bnzl Ph-Et 4-OH-Bnzl 1.41 482 I IF-723 Bnzl Ph-Et i-Pnt 1.68 446 IIF-724 Bnzl Cbm-E Bnzl 1.24 433 I IF-725 i-Bu Ph-Et i-Bu 1.51 398 IIF-726 i-Bu Np-M i-Bu 1.62 434 I IF-727 i-Bu Ph-Et i-Pnt 1.62 412 IIF-728 i-Bu Cbm-E Np-M 1.37 449 I IF-730 4-OH-Bnzl Np-M i-Pnt 1.62 IIF-731 4-OH-Bnzl Cbm-E Np-M 1.29 499 I IF-732 i-Pnt Bnzl Np-M 1.72 482 IIF-733 i-Pnt Bnzl i-Bu 1.49 398 I IF-734 i-Pnt i-Bu Np-M 1.66 448 IIF-735 i-Pnt i-Bu Bnzl 1.50 398 I IF-736 Ph-Et Bnzl Np-M 1.76 516 IIF-737 Ph-Et Bnzl Bnzl 1.61 466 I IF-738 Ph-Et i-Bu i-Bu 1.49 398 IIF-739 Np-M i-Bu i-Bu 1.66 434 I IF-740 Chm Bnzl i-Pnt 1.69 438 I IF-742Chm i-Bu i-Bu 1.49 390 I IF-743 4-F-Bnzl Bnzl i-Pnt 1.64 450 I IF-744Ph-Et i-Pnt Bnzl 1.65 446 I IF-746 Bnzl Bnzl Ph-Et 1.58 466 I IF-747Bnzl Bnzl Np-M 1.72 502 I IF-751 Bnzl i-Bu 4-OH-Bnzl 1.26 434 I IF-752i-Bu i-Pnt Bnzl 1.50 398 I IF-753 i-Bu Bnzl Np-M 1.64 468 I IF-7554-OH-Bnzl Bnzl i-Pnt 1.42 448 I IF-756 Ph-Et Cbm-E Np-M 1.48 497 IIF-757 Ph-Et i-Pr Np-M 1.65 468 I IF-758 Hdr-E Np-M Bnzl 1.46 456 IIF-759 i-Pnt Np-M Bnzl 1.72 482 I IF-760 Ph-Et Np-M i-Bu 1.71 482 IIF-761 Ph-Et Np-M 4-OH-Bnzl 1.57 532 I IF-762 Np-M i-Pnt Bnzl 1.86 482 IIF-763 Np-M Np-M i-Bu 1.95 518 I IF-764 Chm Np-M Bnzl 1.77 508 I IF-7654-F--Bnzl Np-M Bnzl 1.76 520 I IF-766 Ph-Et Np-M i-Pnt 1.74 497 I IF-767Np-M Np-M i-Pnt 1.96 532 I IF-768 Np-M 4-F-Bnzl Np-M 2.03 570 I IF-769Chm Np-M Ph-Et 1.85 522 I IF-770 Chm Np-M Np-M 1.95 558 I IF-7714-F-Bnzl Np-M Ph-Et 1.80 534 I IF-772 4-F--Bnzl Np-M Np-M 1.95 570 IIF-773 Bnzl Np-M i-Bu 1.67 468 I IF-774 Bnzl Np-M i-Pnt 1.73 482 IIF-775 Bnzl 4-F-Bnzl Np-M 1.75 520 I IF-776 Bnzl Cbm-E Np-M 1.42 483 IIF-777 i-Bu Np-M Ph-Et 1.71 482 I IF-778 i-Bu Np-M Np-M 1.81 518 IIF-779 4-OH-Bnzl Np-M Np-M 1.71 568 I IF-780 Hdr-E i-Bu Ph-Et 1.34 386 IIF-781 Hdr-E i-Bu 4-OH-Bnzl 1.12 388 I IF-782 Ph-Et i-Bu 4-OH-Bnzl 1.44I IF-783 Ph-Et Cbm-E 4-OH-Bnzl 1.03 463 I IF-784 Np-M Bnzl i-Pnt 1.84482 I IF-785 Np-M Bnzl Ph-Et 1.88 516 I IF-786 Np-M Bnzl Np-M 2.03 552 IIF-787 Np-M i-Bu 4-OH-Bnzl 1.40 484 I IF-788 Np-M Cbm-E Np-M 1.65 533 IIF-789 Np-M i-Pr Ph-Et 1.69 468 I IF-790 Np-M i-Pr Bnzl 1.67 454 IIF-791 Chm Bnzl Np-M 1.80 508 I IF-792 Hdr-E i-Pnt i-Bu 1.30 352 IIF-793 Ph-Et Np-M Bnzl 1.80 516 I IF-794 Np-M Np-M Bnzl 2.05 552 IIF-795 Np-M 4-F-Bnzl Bnzl 1.89 520 I IF-796 Hdr-E i-Pnt Ph-Et 1.44 400 IIF-797 Hdr-E Np-M i-Pnt 1.50 436 I IF-798 Hdr-E Np-M Ph-Et 1.50 470 IIF-799 i-Pnt Np-M Ph-Et 1.78 496 I IF-800 i-Pnt 4-F-Bnzl Ph-Et 1.63 464I IF-801 i-Pnt 4-F-Bnzl Np-M 1.71 500 I IF-802 Ph-Et i-Pnt Np-M 1.77 496I IF-803 Ph-Et Np-M Np-M 1.93 566 I IF-804 Ph-Et 4-F-Bnzl Np-M 1.84 534I IF-805 Bnzl Np-M Bnzl 1.72 502 I IF-806 Bnzl Np-M 4-OH-Bnzl 1.45 518 IIF-807 Bnzl 4-F-Bnzl i-Bu 1.55 436 I IF-808 Bnzl 4-F-Bnzl 4-OH-Bnzl 1.39486 I IF-809 Bnzl i-Pnt Np-M 1.79 482 I IF-810 Bnzl Np-M Ph-Et 1.81 516I IF-811 Bnzl 4-F-Bnzl i-Pnt 1.60 450 I IF-812 Bnzl i-Pr Np-M 1.54 454 IIF-814 i-Bu Hxy Bnzl 1.62 412 I IF-815 i-Bu 4-F-Bnzl Bnzl 1.52 436 IIF-816 4-OH-Bnzl i-Pnt Ph-Et 1.51 462 I IF-817 4-OH-Bnzl Bnzl Ph-Et 1.43482 I IF-818 4-OH-Bnzl Bnzl i-Bu 1.32 434 I IF-819 4-OH-Bnzl i-Bu i-Bu1.25 400 I IF-820 i-Pnt Cbx-E Bnzl 0.70 414 C IF-821 Ph-Et Cbx-E i-Pnt0.73 428 C IF-822 Chm Cbx-E Bnzl 0.72 440 C IF-823 4-OH-Bnzl Cbx-E i-Pnt0.61 430 C IF-824 4-OH-Bnzl Cbx-E Ph-Et 0.65 464 C IF-825 Bnzl Cbx-Ei-Bu 0.67 400 C IF-826 Bnzl Cbx-E i-Pnt 0.70 414 C IF-827 Bnzl Cbx-EPh-Et 0.71 448 C IF-828 i-Bu Cbx-E Ph-Et 0.67 414 C IF-829 i-Bu Cbx-E4-OH-Bnzl 0.70 416 C IF-830 i-Pnt Cbx-E Ph-Et 0.72 428 C IF-831 i-PntCbx-E 4-OH-Bnzl 0.59 430 C IF-832 Chm Cbx-E Ph-Et 0.74 454 C IF-833 ChmCbx-E 4-OH-Bnzl 0.62 456 C IF-835 Ph-Et Cbx-E i-Bu 0.69 414 C IF-8364-OH-Bnzl Cbx-E i-Bu 0.58 416 C

Com- Retention pound RT Mass Measument number R₁ R₂ R₃ R₄ (min) (M + H)⁺condition IF-837 Bnzl Np-M i-Bu H 1.127 468 B IF-838 Bnzl 4- i-Bu H1.14  486 B (trifluoromethyl) benzyl IF-839 4-Cl-Bnzl Bnzl i-Bu H 1.13 452 B IF-840 3-Cl-Bnzl Bnzl i-Bu H 1.14  452 B IF-841 4-methoxybenzylBnzl i-Bu H 1.072 448 B IF-842 4-methylbenzyl Bnzl i-Bu H 1.097 432 BIF-843 i-Pnt i-Bu Bnzl H 1.278 398 B IF-844 i-Bu i-Bu 4-Cl-Bnzl H 1.275418 B IF-845 i-Bu i-Pnt Bnzl H 1.082 398 B IF-846 i-Bu 4-Cl-Bnzl i-Bu H1.085 418 B IF-847 4-hydroxybenzyl Bnzl i-Bu H 1.187 434 B IF-848 4-Bnzl i-Bu H 1.097 461 B (dimethylamino) benzyl IF-849 4-(tert- Bnzl i-BuH 1.175 474 B butyl)benzyl IF-850 i-Bu Bnzl i-Pnt H 1.075 398 B IF-851i-Pnt Bnzl i-Bu H 1.29  398 B IF-852 4- Bnzl i-Bu H 1.18  502 B(trifluoromethyl) benzyl IF-853 4-ethoxybenzyl Bnzl i-Bu H 1.112 462 BIF-854 Bnzl naphthalen-2- i-Bu H 1.142 468 B ylmethyl IF-8554-methylbenzyl Bnzl i-Bu ethyl 1.172 460 B IF-856 4-methylbenzyl Bnzli-Bu i-Bu 1.303 488 B IF-857 4-methylbenzyl Bnzl i-Bu acetyl 1.187 474 BIF-858 4-methylbenzyl Bnzl i-Bu 3-methyl- 1.247 516 B butanoyl IF-8594-methylbenzyl Bnzl i-Bu 2-phenyl- 1.253 550 B acetyl IF-8604-methylbenzyl Bnzl i-Bu methoxy- 1.23  490 B carbonyl IF-8614-methylbenzyl Bnzl i-Bu 2-methyl- 1.292 532 B propoxy- carbonyl IF-8624-methylbenzyl Bnzl i-Bu benzyl- 1.297 566 B oxy- carbonyl IF-8634-methylbenzyl Bnzl i-Bu amino- 1.157 475 B carbonyl IF-8644-methylbenzyl Bnzl i-Bu N-benzyl- 1.252 565 B amino- carbonyl IF-865Bnzl pyridin-4- i-Bu H 1.11  419 B ylmethyl IF-866 4- 3-hydroxybenzyli-Bu H 1.223 477 B (dimethylamino) benzyl IF-867 4- 4-hydroxybenzyl i-BuH 1.208 477 B (dimethylamino) benzyl IF-868 2-hydroxyethyl4-fluorobenzyl Np-M H 0.76  474 C IF-869 4-methoxybenzyl Bnzl Bnzl H0.83  482 C IF-870 4-methoxybenzyl Bnzl Bnzl tert- 1.01  582 C butoxy-carbonyl IF-871 ethyl Bnzl Bnzl tert- 0.94  490 C butoxy- carbonylIF-872 phenethyl Bnzl 2-(tert- H 0.95  534 C butyldimethyl-silyloxy)ethyl IF-873 cyclopentyl- 4-(tert- 2-(tert- H 0.93  554 Cmethyl butoxy)benzyl butoxycarbonyl) ethyl IF-874 4-nitrobenzyl 4-(tert-2-(tert- H 0.97  607 C butoxy)benzyl butoxycarbonyl) ethyl IF-875phenethyl Bnzl 2-hydroxyethyl H 0.72  420 C IF-876 cyclopentyl- 4-(tert-2-(tert- methoxy- 1.03  612 C methyl butoxy)benzyl butoxycarbonyl)carbonyl ethyl IF-877 cyclopentyl- 4-hydroxybenzyl 2-carboxyethylmethoxy- 0.71  500 C methyl carbonyl IF-878 cyclopentyl- 4-hydroxybenzyl2-carboxyethyl H 0.64  442 C methyl IF-879 phenethyl Bnzl 2-hydroxyethylmethoxy- 0.8  478 C carbonyl IF-880 4-aminobenzyl 4-(tert- 2-(tert-formyl 0.89  605 C butoxy)benzyl butoxycarbonyl) ethyl IF-881 4-4-(tert- 2-(tert- formyl 1    701 C (cyclopentyl- butoxy)benzylbutoxycarbonyl) carbonylamino) ethyl benzyl IF-882 4- 4-(tert- 2-(tert-formyl 1.07  687 C (cyclopentyl- butoxy)benzyl butoxycarbonyl)methylamino) ethyl benzyl IF-883 4-(cyclopentyl- 4-hydroxybenzyl2-methoxy- H 0.81  561 C methylamino) carbonylethyl benzyl IF-884 4-4-hydroxybenzyl 2-carboxylethyl H 0.75  547 C (cyclopentyl- methylamino)benzyl

Com- Retention pound RT Mass Measument number R₁ R_(2A) R_(2B) R₃ R₄(min) (M + H)⁺ condition IF-885 i-Bu H 4-Cl-Bnzl Ph-Et H 1.99 466   B1IF-886 i-Bu H 3-Cl-Bnzl Ph-Et H 1.98 466   B1 IF-887 i-Bu H 4-MeO-BnzlPh-Et H 1.75 462   B1 IF-888 i-Bu H 4-Me-Bnzl Ph-Et H 1.92 446   B1IF-889 i-Bu H 2-Npm Ph-Et H 2.07 482   B1 IF-890 i-Bu H Bnzl Ph-Pr H1.89 446   B IF-891 i-Bu H 3-Cl-Bnzl Ph-Pr H 1.16 480   B IF-892 i-Bu H3-F-Bnzl Ph-Pr H 1.14 464   B IF-893 i-Bu H 3-Me-Bnzl Ph-Pr H 1.13 460  B IF-894 i-Bu H 3-MeO-Bnzl Ph-Pr H 1.10 476   B IF-895 i-Bu H 3-Cl-BnzlPh-Bu H 1.16 494   B IF-896 i-Bu H 3-F-Bnzl Ph-Bu H 1.12 478   B IF-897i-Bu H 3-Me-Bnzl Ph-Bu H 1.16 474   B IF-898 i-Bu H 3-MeO-Bnzl Ph-Bu H1.12 491   B IF-899 i-Bu H Bnzl Ph-Bu H 1.13 460   B IF-900 i-Pnt H3-F-Bnzl Ph-Pr H 1.14 478   B IF-901 1-Npm H pentyl Ph-Et H 0.92 496   CIF-902 1-Npm H cyclohexyl Ph-Et H 0.92 508   C IF-903 1-Npm Hcyclopentyl Ph-Et H 0.90 494   C IF-904 1-Npm H Hxy 4- H 0.99 524   Cmethylphenethyl IF-905 1-Npm H Hxy 2-(naphthalen-2- H 1.02 560   Cyl)ethyl IF-906 1-Npm H heptyl Ph-Et H 1.00 524   C IF-907 1-Npm H Hxy4-isopropyl- H 1.05 552   C phenethyl IF-908 1-Npm H Hxy cyclohexylethylH 1.03 516   C IF-909 i-Bu H Ph-Et Ph-Et H 1.87 444   B1 IF-910 Chm HtBuO-E 1-Npm H 0.87 518   C IF-911 tBuO-E H Ph-Et 1-Npm H 0.88 526   CIF-912 Ph-Et H Hxy 1-Npm H 0.95 510   C IF-913 tBuO-E H 4-fluoro- 1-NpmH 0.89 544.4 C phenethyl IF-914 Hdr-E H 4-fluoro- 1-Npm H 0.77 488.3 Cphenethyl IF-915 3-tert- H 4-F-Bnzl 1-Npm H 0.89 544.4 C butoxy- propylIF-916 tBuO-E H 4-Cl-Bnzl 1-Npm H 0.9  546.3 C IF-917 3-hydroxy- H4-F-Bnzl 1-Npm H 0.76 488.3 C propyl IF-918 Hdr-E H 4-Cl-Bnzl 1-Npm H0.78 490.3 C IF-919 1-Npm H Hxy 3- H 0.99 524.4 C methylphenethyl IF-9201-Npm H β-hydroxy- Ph-Et H 0.84 546.4 C phenethyl IF-921 1-Npm Hα-hydroxy- Ph-Et H 0.88 560.4 C methyl- phenethyl IF-922 1-Npm Hα-hydroxy- Ph-Et H 0.85 560.4 C methyl- phenethyl IF-923 4-Nt-Bnzl HBnzl tBOC-E H 0.86 535   C IF-924 4-Nt-Bnzl H Bnzl tBOC-E ethoxy- 0.94607   C carbonyl IF-925 1-Npm H 4-F-Bnzl 2-OH-Et H 0.73 474.3 C IF-9264-tBuO- H Bnzl i-Bu H 0.91 490.4 C Bnzl IF-927 4-tBuO- H i-Bu Bnzl H0.88 490.4 C Bnzl IF-928 2-OtBu-Et H Bnzl 1-Npm H 0.85 512.4 C IF-9292-OH-Et H Bnzl 1-Npm H 0.74 456.3 C IF-930 4-OH-Bnzl H i-Bu Bnzl H 0.73434.3 C IF-931 1-Npm H 4-F-Bnzl 2-OTBS-Et H 1.01 588.4 C ¹(M − H)⁻

Example 2 Assay Method for Anti-Rabies Virus Activity

Each tested compound prepared as a 10 mM with DMSO was first diluted to100 μM or 40 μM with 10% fetal bovine serum-supplemented Eagle's minimalessential medium (hereinafter, medium), and further diluted with themedium to the final concentration of interest. Fifty microlitter of thediluted medium was added dropwise to each well of a 96-well plate.Furthermore, 50 μL of medium comprising 4×10² infectious units of therecombinant rabies virus 1088 strain expressing Gaussia Luciferase(GLuc) (1088/GLuc) and 4×10⁴ Neuro-2a cells were added to each well. Theplate was shaken for 30 seconds with a multiple microplate mixer NS-4P(AS ONE Corporation) and then cultured for 3 days at 37° C. in thepresence of 5% CO₂. After incubation, 25 μL of coelenterazine, which isa substrate of the luciferase, was added dropwise to each well of theplate, and the plate was immediately loaded into a luminescent platereader LuMate (Awareness Technology) and shaken for 10 seconds. Therelative light unit (RLU) was then measured.

The synthesized compounds were tested. It was found that the compoundsdescribed in Table 5 exhibited the higher anti-rabies virus activitycompared to T-705 (generic name: Favipiravir) (IC₅₀=30 μM), which isexamined as an anti-rabies antiviral drug.

The compounds are classified as A if IC₅₀ is 5 μM or less, B if greaterthan 5 μM and less than or equal to 10 μM, and C if greater than 10 μMand less than 30 μM. The ‘na’ indicates not applicable.

TABLE 5 Compound number Name of compound IC₅₀ (μM) IB-3(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-N,1- 19.6diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-4 (3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-N,7-19.2 diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-5 (3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1,7-18.2 diisobutyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-9 (3S*,3aS*,6R*,7R*,7aS*)-N,7-dibenzyl-1-17.0 isopentyloctahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-12(3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-7-isobutyl-N- 15.5phenethyloctahydro-3aH-3,6-methanopyrrolo[3,2- b]pyridine-3a-carboxamideIB-13 (3S*,3aS*,6R*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3- 14.3methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IB-15(3S*,3aS*,6R*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(3- 15.9methylbenzyl)octahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IF-1 (3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-12.6 isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-6 (3S*,3aS*,6S*,7R*,7aS*)-1,7-dibenzyl-N-16.3 isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-7 (3S*,3aS*,6S*,7R*,7aS*)-N,1-dibenzyl-7-8.5 isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-9 (3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-1-15.6 isopentyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-11(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7- 17.5phenethyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIF-13 (3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(3- 13.1methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-14(3S*,3aS*,6S*,7R*,7aS*)-N-benzyl-1-isobutyl-7-(4- 14.1methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-15(3S*,3aS*,6S*,7R*,7aS*)-7-benzyl-1-isobutyl-N-(3- 17.1methylbenzyl)octahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-20 (3S*,3aS*,6S*,7R*,7aS*)-1-benzyl-N-(3,4-11.6 dichlorobenzyl)-7-isobutyloctahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide IF-69(3S*,3aS*,6S*,7R*,7aS*)-N,7-dibenzyl-4-ethyl-1- 16.5isobutyloctahydro-6H-3,6-methanopyrrolo[3,2- c]pyridine-6-carboxamideIIB-4 (3S*,3aS*,6R*,7R*,7aS*)-1-benzyl-N,7-diisobutyl- 8.91,2,3,6,7,7a-hexahydro-3aH-3,6-methanopyrrolo[3,2-b]pyridine-3a-carboxamide IIF-16(3S*,3aR*,6S*,7R*,7aR*)-7-benzyl-1-isobutyl-N-(4- 28.7methylbenzyl)-1,2,3,3a,7,7a-hexahydro-6H-3,6-methanopyrrolo[3,2-c]pyridine-6-carboxamide Table. Anti-rabies activityof compound of formula IB (A: IC₅₀ ≤ 5 μM, B: 5 μM < IC₅₀ ≤ 10 μM, C: 10μM < IC₅₀ < 30 μM) Anti- Compound rabies number R₁ R₂ R₃ R₄ activityIB-3 i-Bu i-Bu Bnzl H C IB-4 Bnzl i-Bu i-Bu H C IB-5 i-Bu Bnzl i-Bu H CIB-9 i-Pnt Bnzl Bnzl H C IB-12 i-Bu phenethyl Bnzl H C IB-13 i-Bu Bnzl3- H C methylbenzyl IB-15 i-Bu 3- Bnzl H C methylbenzyl IB-42 Np-M BnzlBnzl H C IB-81 carbamoylmethyl 1- i-Bu H C naphthylmethyl IB-82carbamoylmethyl 1- Bnzl H C naphthylmethyl IB-83 carbamoylmethyl 1- 4- HC naphthylmethyl hydroxybenzyl IB-84 carbamoylmethyl 1- i-Pnt H Cnaphthylmethyl IB-86 carbamoylmethyl 2- i-Bu H C phenylethyl IB-87carbamoylmethyl 2- Bnzl H A phenylethyl IB-89 carbamoylmethyl 2- i-Pnt HA phenylethyl IB-90 carbamoylmethyl 1- 1- H A naphthylmethylnaphthylmethyl IB-92 carbamoylmethyl 4- Bnzl H C fluorobenzyl IB-95carbamoylmethyl 4- 2- H A fluorobenzyl phenylethyl IB-96 carbamoylmethyl4- 1- H C fluorobenzyl naphthylmethyl IB-97 carbamoylmethyl 2- 1- H Aphenylethyl naphthylmethyl IB-102 carbamoylmethyl i-Pnt 2- H Aphenylethyl IB-103 carbamoylmethyl i-Pnt 1- H C naphthylmethyl IB-105carbamoylmethyl hexyl Bnzl H C IB-108 carbamoylmethyl hexyl i-Pnt H CIB-109 carbamoylmethyl hexyl 2- H C phenylethyl IB-110 carbamoylmethylhexyl 1- H A naphthylmethyl IB-130 carbamoylmethyl Bnzl 2- H Cphenylethyl IB-164 3- 1- i-Bu H A guanidinopropyl naphthylmethyl IB-1743- hexyl 2- H C guanidinopropyl phenylethyl IB-176 3- isopropyl i-Bu H Cguanidinopropyl IB-179 3- isopropyl 2- H C guanidinopropyl phenylethylIB-182 3- 4- Bnzl H C guanidinopropyl fluorobenzyl IB-187 i-Bu i-Bu 3- HC guanidinopropyl IB-192 i-Bu i-Pnt 3- H A guanidinopropyl IB-198 Bnzli-Bu 3- H C guanidinopropyl IB-203 4- i-Bu 3- H C hydroxybenzylguanidinopropyl IB-207 4- 4- 3- H C hydroxybenzyl fluorobenzylguanidinopropyl IB-247 Bnzl phenethyl 3- H C guanidinopropyl IB-249 Bnzlhexyl 3- H C guanidinopropyl IB-250 Bnzl 4- 3- H C fluorobenzylguanidinopropyl IB-256 phenethyl hexyl 3- H C guanidinopropyl IB-260 4-Bnzl 3- H C fluorobenzyl guanidinopropyl IB-262 4- phenethyl 3- H Cfluorobenzyl guanidinopropyl IB-274 Bnzl 3-amino-3- i-Pnt H C oxopropylIB-276 Bnzl 3- Bnzl H C guanidinopropyl IB-279 Bnzl 3- phenethyl H Cguanidinopropyl IB-280 Bnzl 3- Np-M H C guanidinopropyl IB-300 3- BnzlNp-M H C guanidinopropyl IB-327 3- phenethyl Np-M H C guanidinopropylIB-342 phenethyl 3-amino-3- i-Pnt H C oxopropyl IB-344 phenethyl 3- BnzlH C guanidinopropyl IB-346 phenethyl 3- i-Pnt H C guanidinopropyl IB-347phenethyl 3- Np-M H C guanidinopropyl IB-349 Np-M 3-amino-3- i-Pnt H Aoxopropyl IB-350 Np-M 3- i-Bu H C guanidinopropyl IB-351 Np-M 3- Bnzl HC guanidinopropyl IB-353 Np-M 3- i-Pnt H A guanidinopropyl IB-354 Np-M3- phenethyl H A guanidinopropyl IB-357 cyclohexylmethyl 3-amino-3-i-Pnt H C oxopropyl IB-361 cyclohexylmethyl 3- i-Pnt H C guanidinopropylIB-362 cyclohexylmethyl 3- phenethyl H A guanidinopropyl IB-365 4-3-amino-3- i-Pnt H C fluorobenzyl oxopropyl IB-369 4- 3- i-Pnt H Cfluorobenzyl guanidinopropyl IB-372 2- i-Bu i-Pnt H C hydroxyethylIB-378 i-Bu i-Bu i-Pnt H A IB-381 i-Pnt 2- Np-M H C carboxyethyl IB-3844- 2- Np-M H C fluorobenzyl carboxyethyl IB-386 i-Pnt 4- 2- H Cfluorobenzyl carboxyethyl IB-389 cyclohexylmethyl Np-M 2- H Ccarboxyethyl IB-390 4- Np-M 2- H C fluorobenzyl carboxyethyl IB-392 2-Np-M i-Bu H C carboxyethyl IB-394 2- 4- Bnzl H C carboxyethylfluorobenzyl IB-398 2- Np-M i-Pnt H C carboxyethyl IB-399 2- 4- i-Pnt HC carboxyethyl fluorobenzyl IB-402 2- 4- i-Pnt H C carboxyethylhydroxybenzyl IB-410 4- 2- Np-M H C hydroxybenzyl carboxyethyl IB-417Np-M 4- Np-M H C hydroxybenzyl IB-425 2- Np-M 2- H C hydroxyethylcarboxyethyl IB-426 i-Pnt Np-M hydroxymethyl H A IB-430 2- i-Buphenethyl H A carboxyethyl IB-431 2- i-Bu hydroxymethyl H C carboxyethylIB-449 phenethyl 4- i-Bu H C hydroxybenzyl IB-458 4- 4- i-Bu H Cfluorobenzyl hydroxybenzyl IB-459 Np-M 2- 4- H C hydroxyethylhydroxybenzyl IB-461 phenethyl 2- i-Pnt H C hydroxyethyl IB-464 Bnzl 4-i-Bu H A hydroxybenzyl IB-465 i-Bu 4- i-Pnt H C hydroxybenzyl IB-470 2-4- Np-M H C hydroxyethyl hydroxybenzyl IB-476 2- hexyl Bnzl H Ahydroxyethyl IB-477 2- hexyl i-Bu H A hydroxyethyl IB-478 2- hexyl 4- HC hydroxyethyl hydroxybenzyl IB-479 2- 4- Bnzl H C hydroxyethylfluorobenzyl IB-481 i-Pnt 4- 4- H A fluorobenzyl hydroxybenzyl IB-484cyclohexylmethyl phenethyl Bnzl H A IB-490 2- hexyl i-Pnt H Ahydroxyethyl IB-492 2- 4- phenethyl H A hydroxyethyl fluorobenzyl IB-495i-Bu phenethyl i-Bu H A IB-498 i-Bu 4- 4- H A fluorobenzyl hydroxybenzylIB-499 4- 4- i-Bu H A hydroxybenzyl fluorobenzyl IB-501 4- isopropyli-Pnt H A hydroxybenzyl IB-502 4- isopropyl Np-M H A hydroxybenzylIB-505 i-Pnt Bnzl 2- H C carboxyethyl IB-508 phenethyl i-Bu 2- H Ccarboxyethyl IB-510 cyclohexylmethyl i-Bu 2- H C carboxyethyl IB-515 2-4- phenethyl H C carboxyethyl hydroxybenzyl IB-516 2- 4- Np-M H Ccarboxyethyl hydroxybenzyl IB-520 Np-M 3-amino-3- i-Bu H A oxopropylIB-521 Np-M 3-amino-3- 4- H C oxopropyl hydroxybenzyl IB-522cyclohexylmethyl 3-amino-3- Np-M H C oxopropyl IB-525 4- 3-amino-3- Np-MH C fluorobenzyl oxopropyl IB-527 2- Np-M 4- H C hydroxyethylhydroxybenzyl IB-531 2- phenethyl i-Pnt H C hydroxyethyl IB-535 Bnzl3-amino-3- phenethyl H C oxopropyl IB-536 i-Bu phenethyl 4- H Chydroxybenzyl IB-539 i-Bu 3-amino-3- phenethyl H C oxopropyl IB-540 4-phenethyl i-Bu H C hydroxybenzyl IB-541 4- Np-M i-Bu H A hydroxybenzylIB-544 4- phenethyl i-Pnt H C hydroxybenzyl IB-549 2- 4- 4- H Chydroxyethyl fluorobenzyl hydroxybenzyl IB-551 i-Pnt hexyl i-Bu H AIB-553 i-Pnt 4- i-Bu H A fluorobenzyl IB-562 Bnzl hexyl Bnzl H C IB-568Bnzl 4- phenethyl H C fluorobenzyl IB-574 4- i-Pnt Bnzl H Chydroxybenzyl IB-575 2- i-Bu Np-M H C carboxyethyl IB-576 i-Pnt 4-phenethyl H C hydroxybenzyl IB-577 i-Pnt 4- Bnzl H C hydroxybenzylIB-581 cyclohexylmethyl 4- i-Bu H C hydroxybenzyl IB-582 4- 4- i-Pnt H Cfluorobenzyl hydroxybenzyl IB-583 4- 4- Bnzl H C fluorobenzylhydroxybenzyl IB-585 2- Np-M i-Bu H C hydroxyethyl IB-588 Np-M 2- Bnzl HA hydroxyethyl IB-593 phenethyl 2- Np-M H C hydroxyethyl IB-602 Bnzl 2-Np-M H C hydroxyethyl IB-610 2- 2- Np-M H C hydroxyethyl carboxyethylIB-611 i-Pnt 2- i-Bu H C carboxyethyl IB-613 cyclohexylmethyl 2- i-Pnt HC carboxyethyl IB-614 cyclohexylmethyl 2- Np-M H C carboxyethyl IB-616Bnzl 2- Np-M H C carboxyethyl IB-618 2- Bnzl phenethyl H A hydroxyethylIB-619 2- Bnzl Bnzl H C hydroxyethyl IB-621 2- i-Bu Np-M H Ahydroxyethyl IB-625 phenethyl i-Bu 4- H C hydroxybenzyl IB-630 4- i-Bui-Bu H A fluorobenzyl IB-631 4- i-Bu 4- H C fluorobenzyl hydroxybenzylIB-633 i-Bu i-Bu phenethyl H A IB-636 i-Pnt 3-amino-3- phenethyl H Coxopropyl IB-637 cyclohexylmethyl 3-amino-3- Bnzl H A oxopropyl IB-640phenethyl 2- Bnzl H A hydroxyethyl IB-641 phenethyl 2- i-Bu H Chydroxyethyl IB-642 phenethyl 4- 4- H A fluorobenzyl hydroxybenzylIB-643 Np-M 2- i-Bu H C hydroxyethyl IB-646 cyclohexylmethyl 2- i-Bu H Chydroxyethyl IB-648 cyclohexylmethyl i-Pnt 4- H C hydroxybenzyl IB-6494- 2- Bnzl H C fluorobenzyl hydroxyethyl IB-650 4- 2- i-Bu H Cfluorobenzyl hydroxyethyl IB-656 4- hexyl 4- H A fluorobenzylhydroxybenzyl IB-657 2- 4- i-Pnt H C hydroxyethyl fluorobenzyl IB-658i-Pnt 2- phenethyl H C hydroxyethyl IB-659 i-Pnt 2- Np-M H Ahydroxyethyl IB-663 cyclohexylmethyl 2- phenethyl H A hydroxyethylIB-668 4- 2- i-Pnt H A fluorobenzyl hydroxyethyl IB-669 4- 2- phenethylH C fluorobenzyl hydroxyethyl IB-676 Bnzl 2- Bnzl H C hydroxyethylIB-678 Bnzl i-Pnt 4- H A hydroxybenzyl IB-680 Bnzl 2- i-Pnt H Chydroxyethyl IB-681 Bnzl 2- phenethyl H C hydroxyethyl IB-684 i-Bu i-Pnt4- H C hydroxybenzyl IB-687 i-Bu 2- Np-M H C hydroxyethyl IB-688 i-Bui-Pnt phenethyl H A IB-694 2- Bnzl i-Pnt H C carboxyethyl IB-703 i-Pnt3-amino-3- Np-M H A oxopropyl IB-707 phenethyl 3-amino-3- Bnzl H Aoxopropyl IB-708 phenethyl 3-amino-3- i-Bu H A oxopropyl IB-710cyclohexylmethyl 3-amino-3- phenethyl H A oxopropyl IB-712 4- 3-amino-3-Bnzl H A fluorobenzyl oxopropyl IB-714 2- i-Pnt Bnzl H A hydroxyethylIB-725 4- phenethyl i-Bu H A fluorobenzyl IB-727 2- i-Pnt Np-M H Ahydroxyethyl IB-729 Np-M phenethyl Np-M H A IB-734 Bnzl 3-amino-3- BnzlH C oxopropyl IB-737 i-Bu 3-amino-3- Np-M H C oxopropyl IB-739 4- i-Pnti-Bu H C hydroxybenzyl IB-743 4- 3-amino-3- Np-M H A hydroxybenzyloxopropyl IB-749 i-Pnt Bnzl 4- H C hydroxybenzyl IB-753 i-Pnt i-Bu i-BuH A IB-757 phenethyl Bnzl i-Bu H A IB-759 phenethyl i-Bu Bnzl H A IB-760phenethyl i-Bu i-Bu H A IB-762 Np-M i-Bu i-Bu H A IB-763 Np-M i-Bu 4- HC hydroxybenzyl IB-770 cyclohexylmethyl i-Bu 4- H C hydroxybenzyl IB-7724- Bnzl Bnzl H A fluorobenzyl IB-773 4- Bnzl i-Bu H A fluorobenzylIB-774 4- i-Bu phenethyl H A fluorobenzyl IB-777 Bnzl Bnzl Np-M H AIB-780 i-Bu i-Pnt Bnzl H A IB-783 i-Bu Bnzl 4- H C hydroxybenzyl IB-7864- Bnzl i-Pnt H C hydroxybenzyl IB-787 4- Bnzl i-Bu H C hydroxybenzylIB-804 Np-M Np-M phenethyl H A IB-813 Bnzl 3-amino-3- Np-M H A oxopropylIB-831 2- 4- Np-M H A hydroxyethyl fluorobenzyl IB-864 4-Cl-Bnzl Bnzli-Bu H B IB-865 3-Cl-Bnzl Bnzl i-Bu H B IB-866 4- Bnzl i-Bu H Bmethoxybenzyl IB-867 4- Bnzl i-Bu H B methylbenzyl IB-870 i-Bu i-PntBnzl H C IB-871 i-Bu 4-Cl-Bnzl i-Bu H C IB-873 4- Bnzl i-Bu H B(dimethylamino)benzyl IB-874 4- (tert- Bnzl i-Bu H B butyl)benzyl IB-875i-Bu Bnzl i-Pnt H C IB-876 i-Pnt Bnzl i-Bu H C IB-877 4- Bnzl i-Bu H B(trifluoromethyl)benzyl IB-878 4- Bnzl i-Bu H C ethoxybenzyl IB-879 Bnzlnaphthalen- i-Bu H A 2-ylmethyl IB-880 4- Bnzl i-Bu ethyl A methylbenzylIB-881 4- Bnzl i-Bu i-Bu A methylbenzyl IB-883 4- Bnzl i-Bu 3- Amethylbenzyl methylbutanoyl IB-884 4- Bnzl i-Bu 2- A methylbenzylphenylacetyl IB-885 4- Bnzl i-Bu methoxycarbonyl B methylbenzyl IB-8864- Bnzl i-Bu 2- B methylbenzyl methylpropoxycarbonyl IB-887 4- Bnzl i-Bubenzyloxycarbonyl B methylbenzyl IB-888 4- Bnzl i-Bu aminocarbonyl Cmethylbenzyl IB-889 4- Bnzl i-Bu N- B methylbenzyl benzylaminocarbonylIB-891 4- 3- i-Bu H C (dimethylamino)benzyl hydroxybenzyl IB-892 4- 4-i-Bu H C (dimethylamino)benzyl hydroxybenzyl Table. Anti-rabies activityof compounds of formula XXIB Anti- Compound rabies number R₁ R_(2A)R_(2B) R₃ R₄ activity IB-924 4-Me- H Bnzl i-Bu N- na Bnzlisobutylaminocarbonyl IB-925 i-Bu H 4-Cl-Bnzl Ph-Et H A IB-926 i-Bu H3-Cl-Bnzl Ph-Et H A IB-927 i-Bu H 4-MeO-Bnzl Ph-Et H A IB-928 i-Bu H4-Me-Bnzl Ph-Et H A IB-929 i-Bu H 2-Npm Ph-Et H A IB-930 i-Bu H BnzlPh-Pr H A IB-931 i-Bu H 3-Cl-Bnzl Ph-Pr H A IB-932 i-Bu H 3-F-Bnzl Ph-PrH A IB-933 i-Bu H 3-Me-Bnzl Ph-Pr H A IB-934 i-Bu H 3-MeO-Bnzl Ph-Pr H AIB-935 i-Bu H 3-Cl-Bnzl Ph-Bu H A IB-936 i-Bu H 3-F-Bnzl Ph-Bu H AIB-937 i-Bu H 3-Me-Bnzl Ph-Bu H A IB-938 i-Bu H 3-MeO-Bnzl Ph-Bu H AIB-939 i-Bu H Bnzl Ph-Bu H A IB-940 i-Pnt H 3-F-Bnzl Ph-Pr H A IB-957i-Bu H Ph-Et Ph-Et H A IB-958 i-Bu H 1-Npm Ph-Et H A Table. Anti-rabiesactivity of compounds of formula IF (A: IC₅₀ ≤ 5 μM, B: 5 μM < IC₅₀ ≤ 10μM, C: 10 μM < IC₅₀ < 30 μM) Anti- Compound rabies number R₁ R₂ R₃ R₄activity IF-1 i-Bu Bnzl Bnzl H C IF-6 Bnzl i-Bu Bnzl H C IF-7 Bnzl Bnzli-Bu H B IF-9 i-Pnt Bnzl Bnzl H C IF-11 i-Bu Bnzl phenethyl H C IF-13i-Bu Bnzl 3-methylbenzyl H C IF-14 i-Bu Bnzl 4-methylbenzyl H C IF-15i-Bu 3- Bnzl H C methylbenzyl IF-20 Bnzl 3,4- i-Bu H C dichlorobenzylIF-38 i-Bu Bnzl cyclohexylmethyl H C IF-42 Np-M Bnzl Bnzl H C IF-69 i-BuBnzl Bnzl ethyl C IF-81 2-amino-2- Np-M i-Bu H C oxoethyl IF-822-amino-2- Np-M Bnzl H C oxoethyl IF-84 2-amino-2- Np-M i-Pnt H Coxoethyl IF-85 2-amino-2- Np-M phenethyl H C oxoethyl IF-90 2-amino-2-phenethyl Np-M H C oxoethyl IF-91 2-amino-2- Np-M Np-M H A oxoethylIF-95 2-amino-2- 4- i-Pnt H C oxoethyl fluorobenzyl IF-97 2-amino-2- 4-Np-M H C oxoethyl fluorobenzyl IF-109 2-amino-2- hexyl phenethyl H Coxoethyl IF-110 2-amino-2- hexyl Np-M H A oxoethyl IF-137 2-amino-2- 4-Np-M H A oxoethyl hydroxybenzyl IF-214 i-Pnt isopropyl 3- H Cguanidinopropyl IF-219 phenethyl 3-amino- 2-amino-2- H C 3-oxopropyloxoethyl IF-223 phenethyl Np-M 2-amino-2- H C oxoethyl IF-226 Np-M i-Bu2-amino-2- H C oxoethyl IF-230 Np-M 2- 2-amino-2- H C hydroxyethyloxoethyl IF-235 Np-M i-Bu 3- H C guanidinopropyl IF-236 Np-M Bnzl 3- H Cguanidinopropyl IF-239 Np-M 2- 3- H C hydroxyethyl guanidinopropylIF-243 Np-M hexyl 3- H A guanidinopropyl IF-244 Np-M isopropyl 3- H Aguanidinopropyl IF-245 Np-M 4- 3- H A fluorobenzyl guanidinopropylIF-246 cyclohexylmethyl Bnzl 2-amino-2- H C oxoethyl IF-247cyclohexylmethyl 4- 2-amino-2- H C hydroxybenzyl oxoethyl IF-251cyclohexylmethyl phenethyl 2-amino-2- H C oxoethyl IF-260cyclohexylmethyl hexyl 3- H C guanidinopropyl IF-262 4- i-Bu 2-amino-2-H A fluorobenzyl oxoethyl IF-269 4- phenethyl 2-amino-2- H Cfluorobenzyl oxoethyl IF-274 4- isopropyl 3- H C fluorobenzylguanidinopropyl IF-284 Bnzl Np-M 3- H C guanidinopropyl IF-285 Bnzlhexyl 3- H C guanidinopropyl IF-297 4- Np-M 3- H C fluorobenzylguanidinopropyl IF-298 4- hexyl 3- H C fluorobenzyl guanidinopropylIF-300 i-Bu 3-amino- i-Pnt H C 3-oxopropyl IF-356 3- i-Pnt Np-M H Cguanidinopropyl IF-359 3- phenethyl 4-hydroxybenzyl H C guanidinopropylIF-384 Np-M 3-amino- i-Pnt H C 3-oxopropyl IF-386 Np-M 3- Bnzl H Cguanidinopropyl IF-389 Np-M 3- phenethyl H A guanidinopropyl IF-390 Np-M3- Np-M H C guanidinopropyl IF-411 Bnzl i-Bu i-Pnt H A IF-412 i-Bu i-Bui-Pnt H A IF-413 i-Pnt 2- Np-M H C carboxyethyl IF-416 cyclohexylmethyl2- Np-M H C carboxyethyl IF-417 4- 2- Np-M H C fluorobenzyl carboxyethylIF-419 cyclohexylmethyl Np-M 2-carboxyethyl H C IF-422 2- Np-M i-Pnt H Ccarboxyethyl IF-428 i-Bu 2- Np-M H C carboxyethyl IF-435 Np-M 3-amino-4-hydroxybenzyl H A 3-oxopropyl IF-437 i-Pnt phenethyl i-Bu H C IF-439cyclohexylmethyl phenethyl 4-hydroxybenzyl H A IF-444 2- 2- Np-M H Chydroxyethyl carboxyethyl IF-445 i-Pnt 4- 2-carboxyethyl H Chydroxybenzyl IF-447 cyclohexylmethyl 4- 2-carboxyethyl H Chydroxybenzyl IF-452 2- 2- Np-M H C carboxyethyl hydroxyethyl IF-454 2-i-Bu phenethyl H C carboxyethyl IF-455 2- i-Bu 4-hydroxybenzyl H Ccarboxyethyl IF-458 2- 4- i-Pnt H C carboxyethyl hydroxybenzyl IF-464i-Pnt 4- phenethyl H C hydroxybenzyl IF-465 i-Pnt 4- Np-M H Chydroxybenzyl IF-466 i-Pnt 4- Bnzl H C hydroxybenzyl IF-468 phenethyl 4-i-Pnt H C hydroxybenzyl IF-469 phenethyl 4- Bnzl H C hydroxybenzylIF-470 phenethyl 4- i-Bu H C hydroxybenzyl IF-472 Np-M 4- Bnzl H Ahydroxybenzyl IF-473 Np-M 4- i-Bu H A hydroxybenzyl IF-474cyclohexylmethyl 4- i-Pnt H A hydroxybenzyl IF-475 cyclohexylmethyl 4-phenethyl H C hydroxybenzyl IF-477 cyclohexylmethyl 4- Bnzl H Ahydroxybenzyl IF-478 cyclohexylmethyl 4- i-Bu H A hydroxybenzyl IF-4794- 4- i-Pnt H A fluorobenzyl hydroxybenzyl IF-481 4- 4- Bnzl H Cfluorobenzyl hydroxybenzyl IF-482 4- 4- i-Bu H C fluorobenzylhydroxybenzyl IF-486 cyclohexylmethyl 2- Bnzl H C hydroxyethyl IF-490 4-2- i-Pnt H C fluorobenzyl hydroxyethyl IF-493 Bnzl 4- i-Pnt H Ahydroxybenzyl IF-494 Bnzl 4- Bnzl H C hydroxybenzyl IF-500 i-Bu 4- Np-MH C hydroxybenzyl IF-503 4- isopropyl i-Pnt H A hydroxybenzyl IF-504 4-isopropyl Np-M H C hydroxybenzyl IF-505 Np-M Bnzl 4-hydroxybenzyl H AIF-508 2- 4- Bnzl H C hydroxyethyl fluorobenzyl IF-514 cyclohexylmethylhexyl 4-hydroxybenzyl H A IF-516 2- 4- phenethyl H A hydroxyethylfluorobenzyl IF-525 i-Bu 4- phenethyl H C fluorobenzyl IF-536cyclohexylmethyl 3-amino- Np-M H A 3-oxopropyl IF-539 4- 3-amino- Np-M HA fluorobenzyl 3-oxopropyl IF-542 2- Np-M i-Bu H A hydroxyethyl IF-5432- Np-M 4-hydroxybenzyl H C hydroxyethyl IF-545 i-Pnt phenethyl4-hydroxybenzyl H C IF-546 i-Pnt hexyl i-Bu H C IF-547 i-Pnt 4- Bnzl H Afluorobenzyl IF-548 i-Pnt 4- i-Bu H C fluorobenzyl IF-560 Bnzl hexyli-Bu H A IF-561 Bnzl 4- Bnzl H A fluorobenzyl IF-565 Bnzl 4- phenethyl HA hydroxybenzyl IF-567 i-Bu phenethyl 4-hydroxybenzyl H C IF-568 i-BuNp-M 4-hydroxybenzyl H A IF-569 i-Bu hexyl i-Bu H C IF-576 i-Bu 4-phenethyl H C hydroxybenzyl IF-578 4- Np-M i-Bu H A hydroxybenzyl IF-5804- phenethyl Np-M H C hydroxybenzyl IF-583 i-Pnt hexyl 4-hydroxybenzyl HA IF-584 4- i-Pnt Bnzl H A fluorobenzyl IF-585 4- i-Pnt i-Bu H Afluorobenzyl IF-586 4- phenethyl Bnzl H C fluorobenzyl IF-596 Np-Misopropyl Np-M H C IF-599 i-Pnt hexyl Bnzl H C IF-602 phenethyl hexylBnzl H C IF-603 Np-M 2- Bnzl H C hydroxyethyl IF-604 Np-M 2- i-Bu H Chydroxyethyl IF-606 cyclohexylmethyl 2- i-Bu H C hydroxyethyl IF-610 2-phenethyl Np-M H C hydroxyethyl IF-611 i-Pnt 2- Np-M H C hydroxyethylIF-612 phenethyl 2- Np-M H C hydroxyethyl IF-613 Np-M 2- i-Pnt H Chydroxyethyl IF-614 Np-M 2- Np-M H C hydroxyethyl IF-619cyclohexylmethyl 2- Np-M H C hydroxyethyl IF-620 4- 2- Np-M H Afluorobenzyl hydroxyethyl IF-624 Bnzl 2- Np-M H C hydroxyethyl IF-635i-Pnt i-Bu phenethyl H C IF-639 phenethyl Bnzl i-Bu H A IF-640 phenethylBnzl 4-hydroxybenzyl H C IF-641 phenethyl i-Bu Bnzl H A IF-644cyclohexylmethyl Bnzl i-Bu H A IF-645 cyclohexylmethyl Bnzl4-hydroxybenzyl H C IF-646 cyclohexylmethyl i-Bu Np-M H A IF-649 4- BnzlBnzl H A fluorobenzyl IF-650 4- Bnzl i-Bu H A fluorobenzyl IF-652 4-i-Bu phenethyl H A fluorobenzyl IF-653 4- i-Bu Bnzl H C fluorobenzylIF-654 4- i-Bu i-Bu H A fluorobenzyl IF-656 2- i-Pnt Bnzl H Chydroxyethyl IF-657 phenethyl i-Pnt i-Bu H A IF-658 cyclohexylmethyli-Pnt Bnzl H A IF-659 cyclohexylmethyl i-Pnt i-Bu H C IF-660 2- i-PntNp-M H C hydroxyethyl IF-665 Bnzl i-Pnt Bnzl H A IF-670 Bnzl i-Buphenethyl H A IF-673 i-Bu i-Pnt phenethyl H A IF-674 i-Bu i-Pnt Np-M H CIF-675 i-Bu Bnzl i-Pnt H A IF-679 i-Bu i-Bu phenethyl H A IF-680 i-Bui-Bu Np-M H C IF-684 4- i-Pnt Np-M H C hydroxybenzyl IF-691 benzyl i-Pnti-Bu H C IF-692 Bnzl hexyl 4-hydroxybenzyl H A IF-699 phenethyl 3-amino-i-Bu H C 3-oxopropyl IF-705 i-Pnt Np-M i-Bu H A IF-706 i-Pnt Np-M4-hydroxybenzyl H A IF-707 phenethyl i-Pnt 4-hydroxybenzyl H A IF-708Np-M phenethyl 4-hydroxybenzyl H A IF-709 cyclohexylmethyl i-Pnt4-hydroxybenzyl H C IF-710 cyclohexylmethyl phenethyl Bnzl H A IF-711cyclohexylmethyl phenethyl i-Bu H C IF-714 4- phenethyl i-Bu H Afluorobenzyl IF-715 4- phenethyl 4-hydroxybenzyl H A fluorobenzyl IF-717cyclohexylmethyl phenethyl i-Pnt H A IF-718 cyclohexylmethyl phenethylNp-M H A IF-721 Bnzl phenethyl i-Bu H A IF-722 Bnzl phenethyl4-hydroxybenzyl H A IF-723 Bnzl phenethyl i-Pnt H C IF-725 i-Buphenethyl i-Bu H C IF-726 i-Bu Np-M i-Bu H C IF-727 i-Bu phenethyl i-PntH A IF-730 4- Np-M i-Pnt H C hydroxybenzyl IF-733 i-Pnt Bnzl i-Bu H AIF-734 i-Pnt i-Bu Np-M H A IF-735 i-Pnt i-Bu Bnzl H C IF-738 phenethyli-Bu i-Bu H C IF-739 Np-M i-Bu i-Bu H A IF-740 cyclohexylmethyl Bnzli-Pnt H C IF-742 cyclohexylmethyl i-Bu i-Bu H C IF-743 4- Bnzl i-Pnt H Cfluorobenzyl IF-744 phenethyl i-Pnt Bnzl H A IF-753 i-Bu Bnzl Np-M H CIF-758 2- Np-M Bnzl H A hydroxyethyl IF-778 i-Bu Np-M Np-M H A IF-779 4-Np-M Np-M H C hydroxybenzyl IF-789 Np-M isopropyl phenethyl H C IF-805Bnzl Np-M Bnzl H C IF-807 Bnzl 4- i-Bu H A fluorobenzyl IF-815 i-Bu 4-Bnzl H A fluorobenzyl IF-830 i-Pnt 2- phenethyl H C carboxyethyl IF-837Bnzl Np-M i-Bu H B IF-838 Bnzl 4- i-Bu H C (trifluoromethyl)benzylIF-839 4-Cl-Bnzl Bnzl i-Bu H B IF-840 3-Cl-Bnzl Bnzl i-Bu H B IF-841 4-Bnzl i-Bu H B methoxybenzyl IF-842 4- Bnzl i-Bu H A methylbenzyl IF-845i-Bu i-Pnt Bnzl H C IF-846 i-Bu 4-Cl-Bnzl i-Bu H C IF-848 4- Bnzl i-Bu HB (dimethyl- amino)benzyl IF-849 4-(tert- Bnzl i-Bu H B butyl)benzylIF-850 i-Bu Bnzl i-Pnt H B IF-851 i-Pnt Bnzl i-Bu H C IF-852 4- Bnzli-Bu H B (trifluoro- methyl)benzyl IF-853 4- Bnzl i-Bu H B ethoxybenzylIF-854 Bnzl naphthalen-2- i-Bu H B ylmethyl IF-855 4- Bnzl i-Bu ethyl Bmethylbenzyl IF-856 4- Bnzl i-Bu i-Bu A methylbenzyl IF-859 4- Bnzl i-Bu2- B methylbenzyl phenylacetyl IF-860 4- Bnzl i-Bu methoxycarbonyl Cmethylbenzyl IF-861 4- Bnzl i-Bu 2- B methylbenzyl methylpropoxycarbonylIF-862 4- Bnzl i-Bu benzyloxycarbonyl B methylbenzyl IF-864 4- Bnzl i-BuN- C methylbenzyl benzylaminocarbonyl IF-866 4- 3- i-Bu H C(dimethylamino)benzyl hydroxybenzyl IF-867 4- 4- i-Bu H C(dimethylamino)benzyl hydroxybenzyl Table. Anti-rabies activity ofcompounds of formula XXIF Anti- Compound rabies number R₁ R_(2A) R_(2B)R₃ R₄ activity IF-885 i-Bu H 4-Cl-Bnzl Ph-Et H A IF-886 i-Bu H 3-Cl-BnzlPh-Et H A IF-887 i-Bu H 4-MeO-Bnzl Ph-Et H A IF-888 i-Bu H 4-Me-BnzlPh-Et H A IF-889 i-Bu H 2-Npm Ph-Et H A IF-890 i-Bu H Bnzl Ph-Pr H BIF-891 i-Bu H 3-Cl-Bnzl Ph-Pr H A IF-892 i-Bu H 3-F-Bnzl Ph-Pr H AIF-893 i-Bu H 3-Me-Bnzl Ph-Pr H B IF-894 i-Bu H 3-MeO-Bnzl Ph-Pr H AIF-895 i-Bu H 3-Cl-Bnzl Ph-Bu H A IF-896 i-Bu H 3-F-Bnzl Ph-Bu H AIF-897 i-Bu H 3-Me-Bnzl Ph-Bu H A IF-898 i-Bu H 3-MeO-Bnzl Ph-Bu H BIF-899 i-Bu H Bnzl Ph-Bu H B IF-900 i-Pnt H 3-F-Bnzl Ph-Pr H A IF-909i-Bu H Ph-Et Ph-Et H A Table. Anti-rabies activity of compounds offormula IIB (A: IC₅₀ ≤ 5 μM, B: 5 μM < IC₅₀ ≤ 10 μM, C: 10 μM < IC₅₀ <30 μM) Anti- Compound rabies number R₁ R₂ R₃ activity IIB-4 Bnzl i-Bui-Bu B IIB-83 4-Cl-Bnzl Bnzl i-Bu A IIB-84 3-Cl-Bnzl Bnzl i-Bu A IIB-854-methoxybenzyl Bnzl i-Bu B IIB-86 4-methylbenzyl Bnzl i-Bu B IIB-944-(dimethylamino)benzyl Bnzl i-Bu B IIB-95 4-(tert-butyl)benzyl Bnzli-Bu B IIB-96 4-(trifluoromethoxy)benzyl Bnzl i-Bu B IIB-974-ethoxybenzyl Bnzl i-Bu C IIB-101 4-hydroxybenzyl Bnzl i-Pnt B IIB-102Bnzl naphthalen-2-ylmethyl i-Bu A IIB-103 i-Pnt 4-Cl-Bnzl i-Bu B IIB-104i-Pnt 4-fluorobenzyl i-Bu B Anti-rabies activity of compounds of formulaXXIIB Anti- Compound rabies number R₁ R_(2A) R_(2B) R₃ activity IIF-325i-Pnt H 3-Cl-Bnzl Bnzl A IIF-328 i-Pnt H 4-Me-Bnzl Bnzl A IIF-329 i-PntH 4-MeO-Bnzl Bnzl A IIB-329 Me H quinolin-8-ylethyl Bnzl A IIB-330 Me Hquinolin-5-ylethyl Bnzl A IIB-331 i-Bu H 4-Cl-Bnzl Ph-Et A IIB-332 i-BuH 3-Cl-Bnzl Ph-Et A IIB-333 i-Bu H 4-MeO-Bnzl Ph-Et A IIB-334 i-Bu H4-Me-Bnzl Ph-Et A IIB-335 i-Bu H 2-Npm Ph-Et A IIB-336 i-Bu H Bnzl Ph-PrA IIB-337 i-Bu H 3-Cl-Bnzl Ph-Pr A IIB-338 i-Bu H 3-F-Bnzl Ph-Pr AIIB-339 Cpm H 4-OH-Bnzl 2-Cbx-Et na IIB-340 i-Bu H 3-Me-Bnzl Ph-Pr AIIB-341 i-Bu H 3-MeO-Bnzl Ph-Pr A IIB-342 i-Bu H 3-Cl-Bnzl Ph-Bu BIIB-343 i-Bu H 3-F-Bnzl Ph-Bu A IIB-344 i-Bu H 3-Me-Bnzl Ph-Bu A IIB-345i-Bu H 3-MeO-Bnzl Ph-Bu A IIB-346 i-Bu H Bnzl Ph-Bu A IIB-347 i-Pnt H3-F-Bnzl Ph-Pr A IIF-327 i-Pnt H 4-F-Bnzl Bnzl A IIF-370 i-Pnt H Ph-EtBnzl A IIF-371 i-Pnt H 1-Npm Bnzl A IIB-374 i-Bu H 4-F-Bnzl Ph-Et AIIB-375 i-Bu H Ph-Et Ph-Et A IIB-376 i-Bu H 1-Npm Ph-Et A IIB-3784-F-Bnzl H 1-Npm i-Bu A Table. Anti-rabies activity of compounds offormula IIF (A: IC₅₀ ≤ 5 μM, B: 5 μM < IC₅₀ ≤ 10 μM, C: 10 μM < IC₅₀ <30 μM) Anti- Compound rabies number R₁ R₂ R₃ activity IIF-16 i-Bu4-Me-Bnzl Bnzl C IIF-83 4-Cl-Bnzl Bnzl i-Bu A IIF-84 3-Cl-Bnzl Bnzl i-BuB IIF-85 4-methoxybenzyl Bnzl i-Bu B IIF-86 4-methylbenzyl Bnzl i-Bu AIIF-94 4-(dimethylamino)benzyl Bnzl i-Bu B IIF-95 4-(tert-butyl)benzylBnzl i-Bu A IIF-96 4-(trifluoromethoxy)benzyl Bnzl i-Bu B IIF-974-ethoxybenzyl Bnzl i-Bu C IIF-101 4-hydroxybenzyl Bnzl i-Pnt B IIF-102Bnzl naphthalen-2-ylmethyl i-Bu A IIF-103 i-Pnt 4-Cl-Bnzl i-Bu B IIF-104i-Pnt 4-fluorobenzyl i-Bu B Table. Anti-rabies activity of compounds offormula XXIIF Anti- Compound rabies number R₁ R_(2A) R_(2B) R₃ activityIIF-325 i-Pnt H 3-Cl-Bnzl Bnzl A IIF-326 i-Pnt H 4-Cl-Bnzl Bnzl AIIF-327 i-Pnt H 4-F-Bnzl Bnzl A IIF-328 i-Pnt H 4-Me-Bnzl Bnzl A IIF-329i-Pnt H 4-MeO-Bnzl Bnzl A IIF-330 i-Bu H 4-Cl-Bnzl Ph-Et A IIF-331 i-BuH 3-Cl-Bnzl Ph-Et A IIF-332 i-Bu H 4-MeO-Bnzl Ph-Et A IIF-333 i-Bu H4-Me-Bnzl Ph-Et A IIF-334 i-Bu H 2-Npm Ph-Et A IIF-335 i-Bu H Bnzl Ph-PrA IIF-336 i-Bu H 3-Cl-Bnzl Ph-Pr A IIF-337 i-Bu H 3-F-Bnzl Ph-Pr AIIF-338 Cpm H 4-OH-Bnzl 2-Cbx-Et na IIF-339 i-Bu H 3-Me-Bnzl Ph-Pr AIIF-340 i-Bu H 3-MeO-Bnzl Ph-Pr A IIF-341 i-Bu H 3-Cl-Bnzl Ph-Bu AIIF-342 i-Bu H 3-F-Bnzl Ph-Bu A IIF-343 i-Bu H 3-Me-Bnzl Ph-Bu A IIF-344i-Bu H 3-MeO-Bnzl Ph-Bu A IIF-345 i-Bu H Bnzl Ph-Bu A IIF-346 i-Pnt H3-F-Bnzl Ph-Pr A IIF-370 i-Pnt H Ph-Et Bnzl A IIF-371 i-Pnt H 1-Npm BnzlA IIF-372 i-Bu H 4-F-Bnzl Ph-Et A IIF-373 i-Bu H Ph-Et Ph-Et A IIF-374i-Bu H 1-Npm Ph-Et A IIF-376 4-F-Bnzl H 1-Npm i-Bu A

Example 3 Efficacy in a Mouse Model of Rabies

In this example, it was tested whether the compound of the presentdisclosure is effective in a rabies mouse model.

(Materials and Methods)

Recombinant rabies virus 1088 strain expressing Red Firefly Luciferase(RFLuc) (1088/RFLuc) was generated by replacing the E2Cr gene of therecombinant virus 1088/E2Cr with the RFLuc gene (Isomura M, Yamada K,Noguchi K, Nishizono A. Near-infrared fluorescent protein iRFP720 isoptimal for in vivo fluorescence imaging of rabies virus infection. JGen Virol. 2017, 98(11): 2689-2698. doi: 10.1099/jgv.0.000950.).Hairless mice (Hos: HR-1, 6-week old, female; Hoshino LaboratoryAnimals) were inoculated with 1×10⁵ infectious units of 1088/RFLucintramuscularly into the right hindlimb and administered the testcompound intraperitoneally for 6 days (Day 0 to Day 6), beginning 1 hourafter inoculation. Actually, 0.5 mL of the solution (2% DMSO, 2% SolutolHS 15, and penicillin/streptomycin-added Dulbecco's phosphate bufferedsaline, available from Nacalai tesque, Sigma-Aldrich, etc.) supplementedwith/without the compound (25 mg/kgBW) was administered twice daily witha 6-hour interval between doses. The inoculated mice were monitored forclinical signs and weighed everyday. The viral dynamics in the treatedmice were observed longitudinally using in vivo imaging as follows; micewere administered D-Luciferin solution (150 mg/kgBW; Wako Pure ChemicalIndustry) intraperitoneally and then imaged (exposure time of 2 minutesand electron-multiplying gain of 300) with the Lumazone imaging system(Nippon Roper) under 2% isoflurane inhalation anesthesia after 15minutes of substrate injection. The obtained images (16-bit TIFF) wereprocessed and analysed using the ImageJ software. The compounds listedin Table 5 that were evaluated in Example 2 were tested as the testcompounds.

(Results)

On days 6 and 8 after virus inoculation, the viral dynamics and theeffect of the test compounds were observed in the mice, where thevirus-driven luciferase luminescence served as an indicator. It wasobserved that the viral propagation and dissemination in the brain andspinal cord were siginificantly suppressed in three of four infectedmice that were given the test compound at 50 mg/kgBW/day for 6 days(Days 0 to 5) compared to the solvent administered group, indicatingthat the antiviral effect of the test compounds on rabies virus was alsoconfirmemd in the infected mouse model. In other words, the compoundslisted in Table 5 that were evaluated in Example 2 were confirmed toattain a significant therapeutic/prophylactic effect. For the nucleicacid analog drug favipiravir (product name: Avigan tablet/ToyamaChemical), which was confirmed to be effective on rabies virus, asignificant prophylactic effect was confirmed in ddY mice given in adose of 300 mg/kgBW/day, but not 100 mg/kgBW/day, for 7 days immediatelyafter viral inoculation (Yamada K, Noguchi K, Komeno T, Furuta Y,Nishizono A. Efficacy of Favipiravir (T-705) in Rabies PostexposureProphylaxis. J Infect Dis. 2016, 213(8):1253-1261.doi:10.1093/infdis/jiv586.). Therefore, the present compoundcan be provided as a novel and highly effective rabies therapeutic agentthat has a different mechanism of action from favipiravir.

Example 4 Anti-Cancer Cell Activity Evaluation Method

The minimum inhibitory concentration (MIC) with respect to cells wasevaluated for compounds in Example 2 with which cell dealth of the host,i.e., mouse neuroblastoma cell strain Neuro-2A, was observed.

Each tested compound prepared as a 10 mM with DMSO was first diluted to100 μM or 40 μM with 10% fetal bovine serum-supplemented medium, andfurther diluted with the medium to the final concentration of interest.Fifty microlitter of the diluted medium was added dropwise to each wellof a 96-well plate. Furthermore, 50 μM of medium comprising 4×10²infectious units of 1088/GLuc and 4×10⁴ Neuro-2a cells were added toeach well. The plate was shaken for 30 seconds with the microplate mixerNS-4P and then cultured for 3 days at 37° C. in the presence of 5% CO₂.After incubation, 25 μL of coelenterazine was added dropwise to eachwell of the plate, and the plate was immediately loaded into theluminescent plate reader LuMate and shaken for 10 seconds. The relativelight unit (RLU) was then measured, and entries in which a cell deathcaused due to virus infection were excluded.

The following tables show the results of evaluating the compounds. Somecompounds were evaluated as a mixture as shown in the following tables.The compounds are classified as a if the minimum inhibitoryconcentration (MIC) is 10 μM or less, b if greater than 10 μM and lessthan or equal to 20 μM, and c if greater than 20 μM and less than orequal to 40 μM. The ‘na’ indicates not applicable.

TABLE 6 Table. Anti-cancer cell activity of compounds of formula XXIB(a: MIC ≤ 10 μM, b: 10 μM < MIC ≤ 20 μM, c: 20 μM < MIC ≤ 40 μM)Anti-cancer Compound cell number R₁ R_(2A) R_(2B) R₃ R₄ activity IB-9244-Me-Bnzl H Bnzl i-Bu N- na isobutylaminocarbonyl IB-925 i-Bu H4-Cl-Bnzl Ph-Et H c IB-926 i-Bu H 3-Cl-Bnzl Ph-Et H b IB-927 i-Bu H4-MeO-Bnzl Ph-Et H c IB-928 i-Bu H 4-Me-Bnzl Ph-Et H c IB-929 i-Bu H2-Npm Ph-Et H b IB-930 i-Bu H Bnzl Ph-Pr H c IB-931 i-Bu H 3-Cl-BnzlPh-Pr H c IB-932 i-Bu H 3-F-Bnzl Ph-Pr H c IB-933 i-Bu H 3-Me-Bnzl Ph-PrH b IB-934 i-Bu H 3-MeO-Bnzl Ph-Pr H b IB-935 i-Bu H 3-Cl-Bnzl Ph-Bu H cIB-936 i-Bu H 3-F-Bnzl Ph-Bu H b IB-937 i-Bu H 3-Me-Bnzl Ph-Bu H cIB-938 i-Bu H 3-MeO-Bnzl Ph-Bu H c IB-939 i-Bu H Bnzl Ph-Bu H c IB-940i-Pnt H 3-F-Bnzl Ph-Pr H c IB-957 i-Bu H Ph-Et Ph-Et H c IB-958 i-Bu H1-Npm Ph-Et H b Table. Anti-cancer cell activity of compounds of formulaXXIF Anti-cancer Compound cell number R₁ R_(2A) R_(2B) R₃ R₄ activityIF-885 i-Bu H 4-Cl-Bnzl Ph-Et H c IF-886 i-Bu H 3-Cl-Bnzl Ph-Et H cIF-887 i-Bu H 4-MeO-Bnzl Ph-Et H c IF-888 i-Bu H 4-Me-Bnzl Ph-Et H naIF-889 i-Bu H 2-Npm Ph-Et H b IF-890 i-Bu H Bnzl Ph-Pr H c IF-891 i-Bu H3-Cl-Bnzl Ph-Pr H b IF-892 i-Bu H 3-F-Bnzl Ph-Pr H c IF-893 i-Bu H3-Me-Bnzl Ph-Pr H c IF-894 i-Bu H 3-MeO-Bnzl Ph-Pr H c IF-895 i-Bu H3-Cl-Bnzl Ph-Bu H b IF-896 i-Bu H 3-F-Bnzl Ph-Bu H b IF-897 i-Bu H3-Me-Bnzl Ph-Bu H b IF-898 i-Bu H 3-MeO-Bnzl Ph-Bu H c IF-899 i-Bu HBnzl Ph-Bu H c IF-900 i-Pnt H 3-F-Bnzl Ph-Pr H c IF-909 i-Bu H Ph-EtPh-Et H na Table. Anti-cancer cell activity of compounds of formulaXXIIB and formula XXIIF Anti-cancer Compound cell number R₁ R_(2A)R_(2B) R₃ activity Mixture of IIB- i-Pnt H 3-Cl-Bnzl Bnzl c 326 andIIF-325 Mixture of IIB- i-Pnt H 4-Me-Bnzl Bnzl c 327 and IIF-328 Mixtureof IIB- i-Pnt H 4-MeO-Bnzl Bnzl na 328 and IIF-329 IIB-329 Me Hquinolin-8- Bnzl na ylethyl IIB-330 Me H quinolin-5- Bnzl na ylethylIIB-331 i-Bu H 4-Cl-Bnzl Ph-Et c IIB-332 i-Bu H 3-Cl-Bnzl Ph-Et bIIB-333 i-Bu H 4-MeO-Bnzl Ph-Et na IIB-334 i-Bu H 4-Me-Bnzl Ph-Et cIIB-335 i-Bu H 2-Npm Ph-Et c IIB-336 i-Bu H Bnzl Ph-Pr c IIB-337 i-Bu H3-Cl-Bnzl Ph-Pr c IIB-338 i-Bu H 3-F-Bnzl Ph-Pr c IIB-339 Cpm H4-OH-Bnzl 2-Cbx-Et na IIB-340 i-Bu H 3-Me-Bnzl Ph-Pr c IIB-341 i-Bu H3-MeO-Bnzl Ph-Pr c IIB-342 i-Bu H 3-Cl-Bnzl Ph-Bu b IIB-343 i-Bu H3-F-Bnzl Ph-Bu c IIB-344 i-Bu H 3-Me-Bnzl Ph-Bu b IIB-345 i-Bu H3-MeO-Bnzl Ph-Bu c IIB-346 i-Bu H Bnzl Ph-Bu b IIB-347 i-Pnt H 3-F-BnzlPh-Pr c Mixture of IIB- i-Pnt H 4-F-Bnzl Bnzl b 371 and IIF-327 Mixtureof IIB- i-Pnt H Ph-Et Bnzl na 372 and IIF-370 Mixture of IIB- i-Pnt H1-Npm Bnzl c 373 and IIF-371 IIB-374 i-Bu H 4-F-Bnzl Ph-Et c IIB-375i-Bu H Ph-Et Ph-Et na IIB-376 i-Bu H 1-Npm Ph-Et c IIB-378 4-F-Bnzl H1-Npm i-Bu b IIF-326 i-Pnt H 4-Cl-Bnzl Bnzl b IIF-330 i-Bu H 4-Cl-BnzlPh-Et c IIF-331 i-Bu H 3-Cl-Bnzl Ph-Et c IIF-332 i-Bu H 4-MeO-Bnzl Ph-Etna IIF-333 i-Bu H 4-Me-Bnzl Ph-Et c IIF-334 i-Bu H 2-Npm Ph-Et c IIF-335i-Bu H Bnzl Ph-Pr na IIF-336 i-Bu H 3-Cl-Bnzl Ph-Pr c IIF-337 i-Bu H3-F-Bnzl Ph-Pr b IIF-338 Cpm H 4-OH-Bnzl 2-Cbx-Et na IIF-339 i-Bu H3-Me-Bnzl Ph-Pr c IIF-340 i-Bu H 3-MeO-Bnzl Ph-Pr na IIF-341 i-Bu H3-Cl-Bnzl Ph-Bu b IIF-342 i-Bu H 3-F-Bnzl Ph-Bu c IIF-343 i-Bu H3-Me-Bnzl Ph-Bu c IIF-344 i-Bu H 3-MeO-Bnzl Ph-Bu c IIF-345 i-Bu H BnzlPh-Bu c IIF-346 i-Pnt H 3-F-Bnzl Ph-Pr c IIF-372 i-Bu H 4-F-Bnzl Ph-Et cIIF-373 i-Bu H Ph-Et Ph-Et c IIF-374 i-Bu H 1-Npm Ph-Et c IIF-3764-F-Bnzl H 1-Npm i-Bu c

[Note]

As disclosed above, the present disclosure is exemplified by the use ofits preferred embodiments. However, it is understood that the scope ofthe present disclosure should be interpreted based solely on the Claims.It is also understood that any patent, any patent application, and anyother references cited herein should be incorporated herein by referencein the same manner as the contents are specifically described herein.The present application is a continuation-in-part application thatclaims priority to Japanese Patent Application No. 2018-153227 filed onAug. 16, 2018 and International Publication No. PCT/JP2019/032032 filedon Aug. 15, 2019 with the Japan Patent Office. The entire contentthereof is incorporated herein by reference.

INDUSTRIAL APPLICABILITY

The present disclosure is useful in the field of rabies and cancertreatment and prophylaxis.

1. A compound represented by formula XXIIF:

or an enantiomer thereof, or a salt thereof, or a solvate thereof,wherein, R₁ and R₃ are each independently, hydrogen, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkynyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, R_(2A) andR_(2B) are each independently, hydrogen, optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.
 2. The compound or an enantiomer thereof, or asalt thereof, or a solvate thereof according to claim 1, wherein thealkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl,and carbonyl of R₁ and R₃ are each independently and optionallysubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from substituent group I, and the alkyl,alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, andcarbonyl, and the non-aryl heterocycle and the heteroaryl ring of R_(2A)and R_(2B) are each independently and optionally substituted with one tothe maximum substitutable number of the same or different substituentsselected from sub stituent group I.
 3. The compound or an enantiomerthereof, or a salt thereof, or a solvate thereof according to claim 1,wherein R₁ and R₃ are each independently, hydrogen, optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted heterocycloalkyl, optionally substituted aryl, optionallysubstituted heteroaryl, or optionally substituted carbonyl, R_(2A) andR_(2B) are each independently, hydrogen, optionally substituted alkyl,optionally substituted cycloalkyl, optionally substitutedheterocycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, or optionally substituted carbonyl, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle or heteroaryl ring, wherein the non-arylheterocycle and the heteroaryl ring are each independently andoptionally substituted.
 4. The compound or an enantiomer thereof, or asalt thereof, or a solvate thereof according to claim 1, wherein R₁ andR₃ are each independently, hydrogen, optionally substituted alkyl,optionally substituted arylalkyl, optionally substituted cycloalkyl,optionally substituted heterocycloalkyl, formyl, optionally substitutedalkylcarbonyl, optionally substituted alkoxycarbonyl, optionallysubstituted arylcarbonyl, optionally substituted aryloxycarbonyl,optionally substituted heteroarylcarbonyl, optionally substitutedheteroaryloxycarbonyl, optionally substituted cycloalkylcarbonyl,optionally substituted cycloalkyloxycarbonyl, optionally substitutedheterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from sub stituent group II,R_(2A) and R_(2B) are each independently, hydrogen, optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted cycloalkyl, optionally substituted heterocycloalkyl, formyl,optionally substituted alkylcarbonyl, optionally substitutedalkoxycarbonyl, optionally substituted arylcarbonyl, optionallysubstituted aryloxycarbonyl, optionally substituted heteroarylcarbonyl,optionally substituted heteroaryloxycarbonyl, optionally substitutedcycloalkylcarbonyl, optionally substituted cycloalkyloxycarbonyl,optionally substituted heterocycloalkylcarbonyl, optionally substitutedheterocycloalkyloxycarbonyl, carbamoyl, optionally substitutedalkylcarbamoyl, optionally substituted alkoxycarbamoyl, optionallysubstituted arylcarbamoyl, optionally substituted heteroarylcarbamoyl,optionally substituted cycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R_(2A) and R_(2B) areoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from sub stituent group II,or R_(2A) and R_(2B), together with the nitrogen atom to which they areattached, forms a 5- to 6-membered non-aryl heterocycle, wherein thenon-aryl heterocycle is optionally substituted with one to the maximumsubstitutable number of the same or different substituents selected fromsubstituent group II.
 5. The compound or an enantiomer thereof, or asalt thereof, or a solvate thereof according to claim 1, wherein R₁ andR₃ are each independently, hydrogen, optionally substituted C₁₋₁₂ alkyl,optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl, optionally substitutedC₃₋₁₀ cycloalkyl, optionally substituted 5- to 10-memberedheterocycloalkyl, formyl, optionally substituted C₁₋₁₂ alkylcarbonyl,optionally substituted C₁₋₁₂ alkoxycarbonyl, optionally substitutedC₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀ aryloxycarbonyl,optionally substituted 5- to 10-membered heteroarylcarbonyl, optionallysubstituted 5- to 10-membered heteroaryloxycarbonyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbonyl, optionally substituted C₃₋₁₀cycloalkyloxycarbonyl, optionally substituted 5- to 10-memberedheterocycloalkylcarbonyl, optionally substituted 5- to 10-memberedheterocycloalkyloxycarbonyl, carbamoyl, optionally substituted C₁₋₁₂alkylcarbamoyl, optionally substituted C₁₋₁₂ alkoxycarbamoyl, optionallysubstituted C₆₋₁₀ arylcarbamoyl, optionally substituted 5- to10-membered heteroarylcarbamoyl, optionally substituted C₃₋₁₀cycloalkylcarbamoyl, or optionally substituted 5- to 10-memberedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from substituent group III,R_(2A) and R_(2B) are each independently, hydrogen, optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₆₋₁₀ aryl C₁₋₁₂ alkyl,optionally substituted C₃₋₁₀ cycloalkyl, optionally substituted 5- to10-membered heterocycloalkyl, formyl, optionally substituted C₁₋₁₂alkylcarbonyl, optionally substituted C₁₋₁₂ alkoxycarbonyl, optionallysubstituted C₆₋₁₀ arylcarbonyl, optionally substituted C₆₋₁₀aryloxycarbonyl, optionally substituted 5- to 10-memberedheteroarylcarbonyl, optionally substituted 5- to 10-memberedheteroaryloxycarbonyl, optionally substituted C₃₋₁₀ cycloalkylcarbonyl,optionally substituted C₃₋₁₀ cycloalkyloxycarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkylcarbonyl, optionallysubstituted 5- to 10-membered heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted C₁₋₁₂ alkylcarbamoyl, optionally substitutedC₁₋₁₂ alkoxycarbamoyl, optionally substituted C₆₋₁₀ arylcarbamoyl,optionally substituted 5- to 10-membered heteroarylcarbamoyl, optionallysubstituted C₃₋₁₀ cycloalkylcarbamoyl, or optionally substituted 5- to10-membered heterocycloalkylcarbamoyl, wherein the groups of R_(2A) andR_(2B) are optionally substituted with one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup III, or R_(2A) and R_(2B), together with the nitrogen atom towhich they are attached, form a 5- to 6-membered non-aryl heterocycle,wherein the non-aryl heterocycle is optionally substituted with one tothe maximum substitutable number of the same or different sub stituentsselected from sub stituent group III.
 6. The compound or an enantiomerthereof, or a salt thereof, or a solvate thereof according to claim 1,wherein R₁ and R₃ are each independently, hydrogen, optionallysubstituted alkyl, optionally substituted arylalkyl, optionallysubstituted cycloalkyl, formyl, optionally substituted alkylcarbonyl,optionally substituted alkoxycarbonyl, optionally substitutedarylcarbonyl, optionally substituted aryloxycarbonyl, optionallysubstituted cycloalkylcarbonyl, optionally substitutedcycloalkyloxycarbonyl, optionally substituted heterocycloalkylcarbonyl,optionally substituted heterocycloalkyloxycarbonyl, carbamoyl,optionally substituted alkylcarbamoyl, optionally substitutedalkoxycarbamoyl, optionally substituted arylcarbamoyl, optionallysubstituted heteroarylcarbamoyl, optionally substitutedcycloalkylcarbamoyl, or optionally substitutedheterocycloalkylcarbamoyl, wherein the groups of R₁ and R₃ areoptionally substituted with one to the maximum substitutable number ofthe same or different sub stituents selected from substituent group III.7. The compound or an enantiomer thereof, or a salt thereof, or asolvate thereof according to claim 1, wherein R₁ is hydrogen, alkyl,C₁₋₁₂ alkyl substituted with one to the maximum substitutable number ofthe same or different substituents selected from the group consisting ofamino, substituted amino, hydroxy, substituted oxy, formyl, substitutedcarbonyl, cycloalkyl, and substituted cycloalkyl, arylalkyl, arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,alkyl, substituted alkyl, hydroxy, substituted oxy, amino, substitutedamino, and nitro, formyl, or substituted carbonyl, wherein thesubstituted amino, substituted oxy, substituted carbonyl, substitutedcycloalkyl, and substituted alkyl in R₁ each independently have one tothe maximum substitutable number of the same or different sub stituentsselected from sub stituent group IV.
 8. The compound or an enantiomerthereof, or a salt thereof, or a solvate thereof according to claim 1,wherein R₁ is hydrogen, alkyl, C₁₋₁₂ alkyl substituted with one to themaximum substitutable number of the same or different substituentsselected from the group consisting of amidinoamino,alkoxycarbonyl-substituted amidinoamino, alkoxy, alkoxycarbonyl,carbamoyl, carboxy, hydroxy, trialkylsilyloxy, and cycloalkyl,arylalkyl, arylalkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, amino,substituted amino, nitro, and hydroxy, formyl, alkylcarbonyl,arylalkylcarbonyl, alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl,carbamoyl, alkylcarbamoyl, or arylalkylcarbamoyl, wherein thesubstituted amino has one to the maximum substitutable number of thesame or different substituents selected from substituent group IV. 9.The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to claim 1, wherein R₃ is hydrogen, alkyl, formyl,substituted carbonyl, or alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of hydroxy, substituted oxy, substituted carbonyl,amino, substituted amino, cycloalkyl, substituted cycloalkyl,heterocycloalkyl, and substituted heterocycloalkyl, arylalkyl, arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, substituted oxy, amino, substituted amino, alkyl, andsubstituted alkyl, heteroarylalkyl, or substituted heteroarylalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substituted alkyl,and substituted heteroarylalkyl in R₃ each independently have one to themaximum substitutable number of the same or different sub stituentsselected from sub stituent group IV.
 10. The compound or an enantiomerthereof, or a salt thereof, or a solvate thereof according to claim 1,wherein R_(2A) and R_(2B) are each independently, hydrogen, alkyl,formyl, substituted carbonyl, alkyl substituted with one to the maximumsubstitutable number of the same or different sub stituents selectedfrom the group consisting of hydroxy, substituted oxy, substitutedcarbonyl, amino, substituted amino, cycloalkyl, substituted cycloalkyl,heterocycloalkyl, and substituted heterocycloalkyl, arylalkyl, arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,nitro, hydroxy, substituted oxy, amino, substituted amino, alkyl, andsubstituted alkyl, heteroarylalkyl, or substituted heteroarylalkyl,wherein the substituted carbonyl, substituted oxy, substituted amino,substituted cycloalkyl, substituted heterocycloalkyl, substituted alkyl,and substituted heteroarylalkyl in R_(2A) and R_(2B) each independentlyhave one to the maximum substitutable number of the same or differentsub stituents selected from sub stituent group IV, or R_(2A) and R_(2B),together with the nitrogen atom to which they are attached, form anon-aryl heterocycle, wherein the non-aryl heterocycle is optionallysubstituted with one or up to the maximum substitutable number of thesame or different substituents selected from substituent group VI. 11.The compound or an enantiomer thereof, or a salt thereof, or a solvatethereof according to claim 1, wherein R₁ is alkyl, alkyl substitutedwith one to the maximum substitutable number of the same or differentsubstituents selected from the group consisting of amidinoamino,carbamoyl, carboxy, hydroxy, and cycloalkyl, arylalkyl, or arylalkylsubstituted with one to the maximum substitutable number of the same ordifferent substituents selected from the group consisting of halogen,alkyl, haloalkyl, alkoxy, haloalkoxy, substituted amino, and hydroxy,wherein the substituted amino has one to the maximum substitutablenumber of the same or different substituents selected from substituentgroup IV.
 12. The compound or an enantiomer thereof, or a salt thereof,or a solvate thereof according to claim 1, wherein R_(2A) is hydrogen,R_(2B) is alkyl, alkyl substituted with one to the maximum substitutablenumber of the same or different substituents selected from the groupconsisting of amidinoamino, carbamoyl, carboxy, hydroxy, and cycloalkyl,arylalkyl, or arylalkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of halogen and alkyl.
 13. The compound or anenantiomer thereof, or a salt thereof, or a solvate thereof according toclaim 1, wherein R3 is alkyl, alkyl substituted with one to the maximumsubstitutable number of the same or different substituents selected fromthe group consisting of amidinoamino, carbamoyl, carboxy, hydroxy, andcycloalkyl, or arylalkyl.
 14. A method for the prophylaxis or treatmentof rabies, comprising administering a therapeutically effective amountof the compound according to claim 1, or a pharmaceutically acceptablesalt thereof, to a subject in need thereof.
 15. A method for theprophylaxis or treatment of cancer, comprising administering atherapeutically effective amount of the compound according to claim 1,or a pharmaceutically acceptable salt thereof, to a subject in needthereof.